J. Org. Chem. 1992,57,1917-1920
1917
Notes Synthesis of Enantiomerically Pure 2,2’-Dihydroxy-1,l’-binaphthyl, 2,2’-Diamino-l,l’-binaphthyl, and 2-Amino-2’-hydroxy-l,l’-binaphthyl. Comparison of Processes Operating as Diastereoselective Crystallization and as Second-OrderAsymmetric Transformation+ Martin SmrEia,*s* Miroslav Lorenc: Vladimh Hanu&# Petr Sedmera,ll and Pave1 Kdovskfi*Pl
Department of Organic Chemistry, Charles University, 12.8 40 Prague 2, Czechoslovakia, The J. Heyro sk4 Institute of Physical Chemistry and Electrochemistry dlSAV, 482 23 Prague 8, Czechoslovakia, Institute of Microbiology CSAV, 142 20 Prague 4, Czechoslovakia, and Department of Chemistry, University of Leicester, Leicester LE1 7RH, England Received June 27,1991
2,2’-Dihydroxy-l,l’-binaphthyl(l)is an established and highly potent chiral ligand,’ both enantiomers of which have been utilized in a variety of synthetic reactions to induce chiralitye2 In contrast, the diamine 2 has received much less attention,b4 while the hydroxy amine 3 was Unknown.
3
2
1
operating in the reaction. In view of the well-known biological activity of amphetamine, it was desirable to explore (1)(a) Noyori, R.;Tomino, I.; Tanimoto, Y. J. Am. Chem. SOC.1979, 101,3129. (b) Noyori, R.;Tomino, I,; Nishizawa, M. J. Am. Chem. SOC. 1979,101,5843.(c) Noyori, R.; Tomino, I.; Tanimoto, Y.; Niahizawa, M. J. Am. Chem. SOC.1984,106,6709.(d) Noyori, R.; Tomino, I.; Yamada, M.; Niehizawa, M. J. Am. Chem. SOC.1984,106,6717. (e) Niehizawa, M.; Yamada, M.; Noyori, R. Tetrahedron Lett. 1981,22,247. (0 Seebach, D.; Beck, A. K.; Rogo, S.; Wonnacott, A. Chem. Ber. 1986,118,3673. (g) Olivero, A. G.; Weidmann, B.; Seebach, D. Helu. Chim. Acta 1981,64, 2485. (h) Ji-Tao, W.; Xinju, F.; Ji-Mm, Q. Synthesis 1989,291. (i) Miyano, S.;Tobita, M.; Nawa, M.;Sato, S.; Hashimoto, H. J. Chem. SOC., Chem. Commun. 1980,1233.(i)Kyba, E.P.; Gokel, G. W.; de Jong, F.; Koga, K.; Sousa, L. R.;Siegel, M. G.; K a p h , L.; Sougah,G. D. Y.; Cram, D. J. J. Org. Chem. 1977,42,4173. (k) Tamai, Y.; Park, H.-C.; Ihuka, K.; Okamura, A,; Miyano, S. Synthesis 1990,222. (1) Gottarelli, G.; Spada, G. P.; Bartach, R.; Solladi6, G.; Zimmermann, R. J. Org. Chem. 1986,51, 589. For the synthesis of pure enantiomers, see: (m) lauskas, R. J. J. Am. Chem. SOC.1989,111, 4953 and references cited therein. (n) Gottarelli, G.; Spada, G. P. J. Org. Chem. 1991,56,!2096.(0) Jacques, J.; Fouquay, C. Org. Synth. 1988,67,1.(p) ”dde,L.K. Org. Synth. 1988,67,13. (2)(a) Morrison, J. D.Asymmetric Synthesis; demic: New York, 1983-1986,Voh. 1-5. (b) KoEoVelj, P.; F. €@%If, J. Synth-ie of Natural Products: Problem of Regroselectruit ; CRC Boca Raton, FL, 1986;Vola. I and 11. (c) N a r d , K. Synt sis 1991,l. (3)(a) Miyamo, S.;Nawa, M.; Mori, A.; Hashimoto, H. Bull. Chem. SOC.Jpn. 1984,57,2171. (b) Kabuto, K.; Yoehida, T.; Yamaguchi, S.; Miyano, S.; Hashimoto, H. J. Org. Chem. 19M,50,3013. (c) Kawakami, Y.; Hiratake, J.; Yamamoto, Y.; Oda, J. J. Chem. SOC.,Chem. Commun. 1984,779. (d) Sakatomo, A.; Yamamoto, Y.; Oda, J. J. Am. Chem. SOC. 1987,109,7188.(e) Lm,J.-H.; Che, Ch.-M.; Lai, T.-F.; Poon, Ch.-K.; Cui, Y. X. J. Chem. Soc., Chem. Commun. 1991,468. (4)For other bmaphthyl derivatives, see, e.g.: (a) Brown, K.; Berry, M. S.; Murdoch, J. R. J. Org. Chem. 1986,50, 4345. (b) Tomoda, S.; Iwaoka, M. J. Chem. SOC.,Chem. Commun. 1988,1283. (c) Tomoda, S.; Fujita, K.; Iwaoka, M. J. Chem. SOC.,Chem. Commun. 1990,129. (d) OMalley, S.; Kodadek, T. Tetrahedron Lett. 1991,22, 2445. (e) De Lucchi, 0.;Fabri, D. Synlett 1990,287. (f) Krishnamurti, R.;Kuivila, H. G.; Shaik, N. S.; Zubieta, J. Organometallics 1991,10,423. (5)SmrEina, M.; Lorenc, M.; H a n d , V.; KoEow&, P. Synlett. 1991, 231. (6)For the q e of quinine aa the fmt chiral ligand in HI reductions, see: (a) Cervinka, 0. Chimia 1969,13,1959. (b) ervinka, 0.; BZtlovakY, 0. Collect. Czech. Chem. Commun. 1967,32,3897. For application of (2S,3R)-(+)-4-(dimethylammo)-1,2-diphenyl-~me~l-2-b~tan01 to asymmetric reductions, see: (c) Yamaguchi, S.; Moaher, H. S. J. Org. Chem. 1973,38,1870.See also: (d) Terashima, S.; T h o , N.; Koga, K. J. Chem. SOC.,Chem. Commun. 1980, 1026. (e) Itauno, S.; Nakano, M.; Miyazaki, K.; Masuda, H.; Ito, K. J. Chem. SOC.,Perkin Trans. 1 1985,2039. For the fmt use of an oxazaborolidhe, see: (0 Hirao, A.; Itauno, S.; Nakahama, 5.;Y d , N. J. Chem. SOC.,Chem. Commun. 1981,315. (g) Itauno, S.;Hirao, A.; Nakahama, S.; Yamazaki, N. J. Chem. Soc., Perkin Trans. 1 1983,1673. (7)(a) Corey, E.J.; Bakshi, R. K.; Shibata, S. J. Am. Chem. SOC.1987, 109,5551. (b) Corey, E.J.; Bakehi, R. K.; Shibata,S.; Chen, C.-P.; Singh, V. K. J. Am. Chem. SOC.1987,109,7925.(c) Corey, E.J.; Shibata, S.; Bakshi, R. K. J. Org. Chem. 1988,53,2861. (d) Corey, E.J.; Gavai, A. V. TetrahedronLett. 1988,29,3201.(e) Corey, E.J.; Jardine, P. Da Silva; Mohri, T. TetrahedronLett. 1988,29,6409.(0 Corey, E.J.; Reichard, G. A. Tetrahedron Lett. 1989,30,5207. (g) Corey, E.J.; Chen, C.-P.; Reichard, G. A. Tetrahedron Lett. 1989, 30,5547. (h) Joehi, N. N.; Srebnik, M.; Brown, H. C. TetrahedronLett. 1989,30,5551.(i) Corey, E. J.; Link, J. 0. Tetrahedron Lett. 1989,30,6275. (i)Corey, E. J.; Jardme, P. Da Silva. Tetrahedron Lett. 1989,30,7297.(k)Corey, E.J.; Link, J. 0. TetrahedronLett. 1990,31,601.(1) Corey, E.;J.; Bakshi, R. K. Tetrahedron Lett. 1990,31,611.(m) Corey, E.J.; Link, J. 0. J. Org. Chem. 1991,56, 442. (n) Corey, E.J.; Naef, R.; Hannon, F. J. J. Am. Chem. SOC.1986,108,7114.(0) Corey, E.J.; Hannon, F. J. Tetrahedron Lett. 1987,28,5233,5237. (p) Corey, E.J.; Yuen, P.-W.; Hannon, F. J.; Wierda, D. A. J. Org. Chem. 1990,55,784. (9) Itauno, S.;Sakurcu, Y.; Ito, K.; Maruyama, T.; Nakahama, S.; Frkhet, J. M. J. J. Org. Chem. 1990,55,304. (r) Mathre, D. J.; Jones, T. K.; Xavier, L. C.; Blacklock, T. J.; Reamer, R. A.; Mohan, J. J.; Jones, E. T. T.; Hoogeteen, K.; h u m , M. W.; Grabowski, E. J. J. J. Org. Chem. 1991,56,751.(e) Brown, J. M.; Lloyd-Jones, G. C. Tetrahedron: Asymmetry 1990,1,869.
+
-5
moHmNH2 4
5
Recently, we have described a facile method for the preparation of racemic hydroxy amine 3 by cross coupling of 2-naphthol (4) and 2-naphthylamine (5) under controlled conditions, using a CuC1,-benzylamine complex in methanol? Simiily, 1 and 2 have been obtained from the homo coupling of 4 or 5, re~pectively.~ Since a number of amino alcohols have proved to be highly efficient as chiral auxiliaries for asymmetric reductionsH and other reaction^?^ it was desirable to develop a method for the preparation of optically active 3. In this paper we report on the syntheak of enantiomerically pure amino alcohol 3 and modified procedures for obtaining pure enantiomers of 1 and 2. Bruaaelohas prepared optically active 1 by coupling of 2-naphthol with a CuCl,-amphetamine complex. He has ale0 provided evidence for the second-order transformation ‘Dedicatedto Profeesor Alois VystrEil on the occasion of his 70th birthday. Charles University. #The J. Heyrovekg Institute. I Institute of Microbiology. University of Leicester.
OO22-3263/92/ 1957-1917$03.O0/0 0 1992 American Chemical Society
9
Y
Notes
1918 J. Org. Chem., Vol. 57, No. 6, 1992 entry 1 2 3 4 ~
5 6 7
8 9 10
11
product
1 1
Table I. Preparation of Optically Active Binaphthyls 1-3 reagent isolation* method" yield: % 14 CuC1,-sparteined P A 42 CuClO-sDarteined S A P 36 B cuC&arteined S 60 B CuC1,-sparteined PS 94 B CuC1,-sparteined P 19 A CuC1,-sparteined 49 S A CuC1,-sparteined PS 95 B CuC1,-sparteined P 43 A CuC12-PhCH(NH2)Mee 42 S A CuClz-PhCH(NHz)Mee 96 PS B CuClz-PhCH(NH,)Mee ~~
deg -34 -7 -34 -20 -27 -134
blD,
88,
%
lW 20' lW 54'
w w
+50
318
