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Cite This: J. Org. Chem. 2018, 83, 9300−9304
Asymmetric Diels−Alder Reaction Involving Dynamic Enantioselective Crystallization Naohiro Uemura,† Seiya Toyoda,† Hiroki Ishikawa,† Yasushi Yoshida,† Takashi Mino,† Yoshio Kasashima,‡ and Masami Sakamoto*,† †
Department of Applied Chemistry and Biotechnology, Graduate School of Engineering, and Molecular Chirality Research Center, Yayoi-cho, Inage-ku, Chiba 265-8522, Japan ‡ Education Center, Faculty of Creative Engineering, Chiba Institute of Technology, Shibazono, Narashino, Chiba 275-0023, Japan
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ABSTRACT: Asymmetric Diels−Alder reaction was achieved under achiral conditions. Reaction of prochiral 2-methylfuran and N-phenylmaleimide in heptane or hexane solution at 80 °C efficiently gave a conglomerate crystal of exo-type Diels−Alder adduct selectively, and continuous suspension of the reaction mixture with glass beads promoted attrition-enhanced deracemization, leading to an optically active exo-adduct in 90% ee.
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INTRODUCTION The Diels−Alder (DA) reaction is one of the most fundamental and illustrious reactions in organic chemistry, providing access to a variety of polycyclic heterocycles.1 Numerous important skeletons have been conveniently constructed by the reaction of various dienes and alkenes.2 Furthermore, this reaction applies to many asymmetric reactions using catalytic asymmetric synthesis3 and chiral auxiliaries,4 leading to optically active cyclic compounds. Naturally, all of these synthetic methodologies require optically active sources such as chiral catalysts or precursors. Recently, asymmetric synthesis involving a reversible reaction and crystal chirality has been developed. Stereoselective crystallization via stereoisomerization from meso to dl-isomers,5 azaMichael addition reactions,6 photoisomerization followed by ring-closing−opening reactions,7 Strecker-type reactions,8 and reversible photodimerization reactions9 have been reported. These reactions were initiated from prochiral precursors, and high optically active crystalline products were conveniently provided under absolutely achiral conditions. These types of reactions all involve dynamic stereoselective crystallization, which is well documented as a total optical resolution method or a crystallization-induced transformation (CIET).10−15 The combination of chiral center generation from prochiral starting materials followed by CIET makes it possible to design absolute asymmetric synthesis involving many types of organic reactions. Up to now, absolute asymmetric synthesis has been limited to the application of physical chiral forces such as circularly polarized light16 and chiral magnetic fields.17 Of course, Soai’s reaction18 and asymmetric synthesis using the chirality of crystals generated by the crystallization of prochiral materials is also considered to be an absolute asymmetric synthesis.19,20 These processes are of great interest to many scientists in a variety of areas because absolute asymmetric © 2018 American Chemical Society
synthesis could support the hypothesis of the origin of homochirality on the primitive Earth.21 Here, we developed a novel absolute asymmetric Diels−Alder reaction by using prochiral maleimide and furan, which is a well-known reversible reaction.22 Specifically, the reaction of asymmetrical 2-methylfuran and symmetrical N-phenylmaleimide was selected (Scheme 1).23 Scheme 1. Diels−Alder Reaction of N-Phenylmaleimide and 2-Methylfuran
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RESULTS AND DISCUSSION Jarosz et al. reported that their DA reaction gave a mixture of exo- and endo-adducts in a ratio of 1.6:1.0 under high-pressure conditions at room temperature.24 Furthermore, the crystal structure of the exo-adduct revealed that the space group was chiral P212121. We reanalyzed the crystal structure both to eliminate the possibility of a polymorphic crystal system and to determine the crystal system of the endo-adduct. When a homogeneous toluene solution of N-phenylmaleimide 2 and 2-methylfuran 1 (1.5 equiv) was left standing overnight, a colorless solid of the exo-adduct was obtained. The filtered exo-3 and endo-4 isolated from the mother liquor were analyzed Received: May 17, 2018 Published: May 28, 2018 9300
DOI: 10.1021/acs.joc.8b01273 J. Org. Chem. 2018, 83, 9300−9304
Article
The Journal of Organic Chemistry by X-ray crystallography. The exo-3 was indeed obtained as a conglomerate of the P212121 space group. The absolute configuration of (−)-exo-3 was determined as (2aS,1R,7S,6aR) (Figure 1), whereas the space group of endo-4 was racemic Pbca (Figure 2).
Scheme 2. Absolute Asymmetric Synthesis by Diels−Alder Reaction Involving Dynamic Stereoselective Crystallization
Figure 1. Perspective view of (−)-exo-3. Ellipsoids were drawn in 50% probability.
Figure 3. Time-dependent reaction course as monitored by 1H NMR spectroscopy. N-Phenylmaleimide (0.02 M) and 2-methylfuran (0.2 M) were reacted in CDCl3 at 60 °C. Blue triangles = unreacted 2; red squares = exo-3; green diamonds = endo-4.
Figure 2. Perspective view of endo-4. Ellipsoids were drawn in 50% probability.
of the reverse reaction under the same conditions. The reverse reaction without catalyst was quite slow; thus, we sought out the best catalyst for activating the reverse reaction using various catalysts such as Zn(OAc)2, TfOH, TsOH, HCl, AcOH, (TfO)3Yb, (TfO)3Eu, p-CF3C6H4B(OH)2, (i-PrO)2TiCl2, TMSNTf2, TMSOTf, and trifluoroacetic acid (TFA). When TMSNTf2 or TMSOTf was used to activate the reverse reaction, 3-methyl-N-phenylphthalimide was obtained quantitatively by C−O bond cleavage followed by aromatization. Other Lewis acids and Brönsted acids were not effective for the reverse DA reaction. Of these catalysts, TFA was the best for accelerating the reversible DA reaction. Figure 4 shows the time course of the retro-DA reaction in which a 0.02 M CDCl3 solution of the exo-adduct was heated at 60 °C with or without TFA (0.2 equiv). Additionally, it was confirmed that TFA did not promote other side reactions. Next, we examined the asymmetric DA reaction involving dynamic enantioselective crystallization. When a heptane solution of N-phenylmaleimide, 2-methylfuran (15.0 equiv), and TFA (0−1.0 equiv) was stirred in the presence of glass beads (Φ = 0.2 mm) at 80 °C in a sealed tube, the crystalline exoadduct appeared quickly. The solution was kept in suspension by stirring for several days at the same temperature, and the change in ee value of exo-3 by attrition-enhanced deracemization was monitored by HPLC using a chiral column, CIRALPAK IA (Daicel Ind.). When we stirred achiral N-phenylmaleimide and 2-methylfuran without TFA in a heptane solution, the induction period until
The DA reaction is well-known to be a concerted electrocycloaddition reaction and to involve a reversible process. We applied this reaction system to the asymmetric synthesis involving dynamic stereoselective crystallization as shown in Scheme 2. The primary DA reaction provides asymmetric chiral materials from prochiral starting substrates, and the racemization of (±)-3 might be promoted by a reversible process. If dynamic stereoselective crystallization by the property of conglomerate crystals is promoted, deracemization will occur, and optically active crystals should be obtained. While the DA reaction generally proceeds endo-selectively, the exo-adduct is more thermodynamically stable. We monitored the reaction course by NMR spectroscopy. Figure 3 shows the reaction course in which 0.02 M of N-phenylmaleimide and 10.0 equiv of 2-methylfuran was reacted at 60 °C in CDCl3. At the early stage of the reaction, both exo- and endo-adducts formed equally; however, after half an hour the endo-adduct gradually decreased, and the ratio of exo to endo reached 8:1 after 6 h. When the reaction was performed on a preparative scale and concentration, the crystalline exo-adduct precipitated and was removed from the reaction system. Finally, the products converged to the exo-adduct, which was isolated in 90% yield accompanied by a trace amount of endo-adduct. These results indicated that the conglomerate crystal of the exo-adduct was formed stereoselectively in this DA reaction system. Another important requirement to apply this asymmetric DA reaction using dynamic stereoselective crystallization is the rate 9301
DOI: 10.1021/acs.joc.8b01273 J. Org. Chem. 2018, 83, 9300−9304
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The Journal of Organic Chemistry
However, the maximum ee value of the solid obtained from the reaction in hexane was slightly lower than that in heptane (86% vs 90%). The solubility of the DA adduct may play an important role in the deracemization with its repeated dissolution and crystallization processes. Hexane had a slightly higher solubility for the DA adduct than heptane at 80 °C in a sealed tube, resulting in the shorter deracemization time and lower ee value of the solid. Chemical yields of the solid in both solvents were 80% after cooling to room temperature. The optical purity of the solid formed by attrition-enhanced deracemization at 80 °C may be much higher than 90% ee. The reaction vessel, a sealed tube, was cooled to room temperature before it was opened because the boiling point of 2-methylfuran was 63 °C. Cooling the reaction mixture introduced crystallization of the racemic DA adduct dissolved in the mother liquor, thus lowering the ee value of the crystals and explaining the capped ee values. However, a chance of a cocrystal or other factor could not be excluded. We were unable to control the handedness of the chirality in the spontaneous crystallization; solids of both types of handedness were obtained in each experiment in almost the same ratio. Primary nucleation gave one small crystal of one enantiomer (conglomerate behavior), followed by rapid propagation due to secondary nucleation of the enantiomer. However, we were able to control the handedness by a seeding method, in which a small amount of crystals was added during the induction period. Furthermore, when we started the attrition-enhanced deracemization from a DA adduct with low ee (5% ee) in heptane with TFA (0.2 equiv) at 80 °C, deracemization started immediately, and the same handedness of the enantiomer as the slightly major stereoisomer could be obtained in 90% ee after 8 days. The use of hexane as the solvent shortened the time for deracemization. We could achieve deracemization up to 86% ee from 5% ee of the starting enantiomer after only 4 days under the same conditions.
Figure 4. Time-dependent course of retro-Diels−Alder reaction. The reaction was applied to the exo-adduct (0.02 M) in CDCl3 solution at 60 °C. Red squares = exo-3; black circles = 2-methylfuran 1; blue triangles = 2. (a) Without TFA and (b) in the presence of TFA (0.2 equiv).
deracemization started was several days. Deracemization began gradually after 15 days, but once initiated, the ee value sharply increased up to 90% ee as shown in Figure 5, line 1. The
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CONCLUSIONS The first example of asymmetric DA reaction was developed involving stereoselective dynamic crystallization via a reversible process. This second-order asymmetric reaction process can be applied to many types of reversible reactions or reactions combined with a racemization process for conglomerate crystals.
Figure 5. Asymmetric Diels−Alder reaction involving attritionenhanced deracemization using glass beads applied to achiral N-phenylmaleimide (100 mg, 0.578 mmol) and 2-methylfuran (710 mg, 8.67 mmol) in hexane or heptane (1.00 mL) at 80 °C with or without TFA (0−1.0 equiv).
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EXPERIMENTAL SECTION
General Information. NMR spectra were recorded in CDCl3 solutions on a Bruker 300 spectrometer operating at 300 and 75 MHz, respectively, for 1H and 13C NMR. Chemical shifts are reported in parts per million (ppm) relative to TMS as an internal standard. IR spectra were recorded on a JASCO FT/IR-230 spectrometer. HPLC analyses were performed on a JASCO HPLC system (JASCO PU-1580 pump, DG-1580-53, LG-2080-02, MD-2015, UV-2075, and CD-2095 detector). X-ray single crystallographic analysis was conducted using a SMART APEX II (Bruker AXS) and APEX II ULTRA (Bruker AXS). Commercially available N-phenylmaleimide and 2-methylfuran were used without further purification. Reaction Conditions for Asymmetric DA Reaction Involving Dynamic Crystallization. In a sealed tube (L = 200 mm, Φ = 25 mm), N-phenylmaleimide (100 mg, 0.578 mmol), 2-methylfuran (710 mg, 8.67 mmol), TFA (0−1.0 equiv), and hexane or heptane (1.0 mL) were stirred with or without glass beads (250 mg) using a stir bar at 80 °C. The crystalline exo-adduct 3 appeared after a few minutes, and the solution was kept in suspension by stirring at 600 rpm for several days at the same temperature. The change of ee value of crystalline 3 was monitored by HPLC using a chiral column, CHIRALPAK IA
attrition of crystals using glass beads was quite effective for deracemization since deracemization was not observed under suspension without glass beads even after 30 days. Furthermore, the induction period could be reduced by the use of TFA as an acid catalyst (lines 2−4). TFA accelerated not only the DA cycloaddition reaction but also the retro-DA reaction without promoting other side reactions. As the amount of TFA increased, there was a tendency toward both a reduction in the induction period and an acceleration in the deracemization, with deracemization starting at the fourth day leading to 90% ee after 11 days (line 4). When using hexane instead of heptane, deracemization proceeded much faster (lines 5−8). Deracemization started after 10 days and reached 86% ee after 19 days without TFA (line 5). TFA influenced both the reduction of induction and deracemization periods, affording an 86% ee of exo-3 after only 5 days by the use of 1.0 equiv of TFA (line 8). 9302
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The Journal of Organic Chemistry (Daicel Ind.): eluent: n-hexane/EtOH = 80/20 (v/v). Finally, crystalline exo-3 was obtained in 80% (118 mg, 0.46 mmol) chemical yield by filtration. The structures of both exo-3 and endo-4 were confirmed by comparison with the reported spectral data.24 (2aS*,1R*,7S*,6aR*)-1-Methyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (exo-3). Colorless prism, Mp: 144− 146 °C; 1H NMR: δ 1.79 (s, 3 H, CH3), 2.86 (d, J = 6.5 Hz, 1 H, 2-H), 3.12 (d, 1 H, J = 6.5 Hz, 6-H), 5.30 (d, J = 1.8 Hz, 1 H, 7-H), 6.37 (d, J = 5.6 Hz, 1 H, 9-H), 6.56 (dd, J = 1.8 and 5.6 Hz, 1 H, 8-H); 7.26−7.29 (m, 2H, Ph), 7.37−7.48 (m, 3H, Ph) 13C{1H} NMR: δ 15.7 (CH3), 49.6, 50.6 (C-2, C-6), 81.1 (C-7), 88.5 (C-1), 126.5, 128.6, 129.0, 131.7, 137.0, 140.7, 174.0, 175.3. (2aS*,1S*,7R*,6aR*)-1-Methyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione (endo-4). Colorless prism, Mp: 115−116 °C; 1H NMR: δ 1.88, (s, 3 H, CH3), 3.27 (d, J = 7.7 Hz, 1 H, 2-H), 3.81 (dd, J = 5.5 and 7.7 Hz, 1 H, 6-H), 5.43 (dd, J = 1.6 and 5.5 Hz, 1 H, 7-H), 6.38 (d, J = 5.7 Hz, 1 H, 9-H), 6.54 (dd, J = 1.6 and 5.7 Hz, 1 H, 8-H); 7.11−7.13 (m, 2H, Ph), 7.35−7.46 (m, 3H, Ph) 13C{1H} NMR: δ 18.4, 48.5, 50.5, 79.4, 88.9, 126.3, 128.7, 129.1, 131.4, 135.1, 137.7, 174.0, 174.1. Single-Crystal X-ray Crystallographic Analysis of (2aS,1R,7S,6aR)1-Methyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5dione ((−)-exo-3). Colorless prism (0.20 × 0.10 × 0.10 mm3), orthorhombic space group P212121, a = 6.7516(3) Å, b = 11.9488(5) Å, c = 15.6306(7) Å, V = 1260.98(10) Å3, Z = 4, λ (Cu Kα) = 1.54178 Å, ρ = 1.345 g/cm3, μ (CuKα) = 0.775 cm, 24869 reflections measured (T = 173 K, 4.658° < θ < 68.227°), nb of independent data collected: 2303; nb of independent data used for refinement: 2302 in the final least-squares refinement cycles on F2; the model converged at R1 = 0.0463, wR2 = 0.1263 [I > 2s(I)], R1 = 0.0464, wR2 = 0.1263 (all data), and GOF = 1.114, H-atom parameters constrained, absolute Flack parameter = 0.09(3) (CCDC 1827990). Single Crystal X-ray Crystallographic Analysis of (2aS*,1S*,7R*,6aR*)-1-Methyl-4-phenyl-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8ene-3,5-dione (endo-4). Colorless prism (0.20 × 0.20 × 0.10 mm3), orthorhombic space group Pbca, a = 12.7547(17) Å, b = 11.3387(15) Å, c = 16.800(2) Å, V = 2429.6(6) Å3, Z = 8, λ (Mo Kα) = 0.71073 Å, ρ = 1.396 g/cm3, μ(Mo Kα) = 0.098 cm, 13062 reflections measured (T = 173 K, 2.4246° < θ < 20.9203°), nb of independent data collected: 2758; nb of independent data used for refinement: 1797 in the final least-squares refinement cycles on F2; the model converged at R1 = 0.0450, wR2 = 0.1001 [I > 2s(I)], R1 = 0.0800, wR2 = 0.1121 (all data), and GOF = 0.968, H-atom parameters constrained (CCDC 1827991).
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ACKNOWLEDGMENTS
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REFERENCES
This work was supported by Grants-in-Aid for Scientific Research (Nos. 25288017, 26410124, and 16H04144) from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of the Japanese Government. Mr. Uemura acknowledges financial support from the Frontier Science Program of Graduate School of Science and Engineering, Chiba University.
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ASSOCIATED CONTENT
S Supporting Information *
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.8b01273. X-ray crystallographic analysis, HPLC analysis, and spectroscopic data for synthesized compounds (PDF) Exo 3 (CIF) Endo 4 (CIF)
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. ORCID
Yasushi Yoshida: 0000-0002-3498-3696 Takashi Mino: 0000-0003-1588-1202 Masami Sakamoto: 0000-0001-9489-2641 Notes
The authors declare no competing financial interest. 9303
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DOI: 10.1021/acs.joc.8b01273 J. Org. Chem. 2018, 83, 9300−9304
