Correction to “Divergent Reactivity of Amino Acid Alkyl Ester

Anil K. Padala, Raju Ranjith Kumar, S. Athimoolam, and Qazi Naveed Ahmed*. Org. Lett. , 2016, 18 (5), pp 1217–1218. DOI: 10.1021/acs.orglett.6b00353...
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Addition/Correction pubs.acs.org/OrgLett

Correction to “Divergent Reactivity of Amino Acid Alkyl Ester Hydrochlorides with 2‑Oxoaldehydes: Role of Selenium Dioxide To Promote Regioselective Synthesis of Imidazoles” Anil K. Padala, Raju Ranjith Kumar, S. Athimoolam, and Qazi Naveed Ahmed* Org. Lett. 2016, 18 (1), 96−99. DOI: 10.1021/acs.orglett.5b03321 S Supporting Information *

T

Table 3. General Substrate Scope of the Reactiona

he following corrections are needed. In the Abstract and TOC graphics, the R and CO2R′ groups should be

Scheme 1

entry

R

R″

yieldb (%)/ time (h)

3p 3q 3r 3s 3t 3u 3v 3w 3x 3y 3z 3aac 3ab 3ac 3ad

Me Me Me Me benzyl isobutyl isobutyl isobutyl isobutyl isobutyl isobutyl ethyl(methyl)sulfane H Me H

3-MePh 4-MePh 4-MeOPh 4-FPh 4-MePh 3-MePh 4-MePh 4-FPh 4-ClPh 4-BrPh 4-MeOPh 4-MePh 5-methylthiophene-2-yl 5-methylthiophene-2-yl 4-NO2Ph

85/3.5 86/3.5 88/3.5 84/3.5 82/3 85/2.5 86/2.5 81/2.5 83/2.5 82/2.5 89/2.5 82/2.5 64/4 86/3 0/24

a

Table 2. Scope of the Reaction

Reaction conditions: 1 (1 mmol), 2 (1.2 mmol), pyridine (1.5 mmol), selenium dioxide (1.2 mmol), and ACN (3 mL). bIsolated yields. c d-isomer.

a

exchanged in the upper amino acid of the structure in the bracketed intermediate “COCH(N1N2) system and in product 3 as shown: entry

R

R′

R″

yieldb (%)/time (h)

3a 3b 3c 3d 3e 3f 3g 3h 3i 3j 3k 3lc 3m 3n 3o

H H H H H H H H Me benzyl isobutyl ethyl(methyl)sulfane H H H

Me Me Me Me Me Me Me Me Me Me Me Me Et Et Et

Ph 4-MePh 3-MePh 4-MeOPh 4-FPh 4-ClPh 4-BrPh 4-HOPh Ph Ph Ph Ph 4-Me 4-F 4-Br

67/4 68/4 66/4 69/4 62/4 64/4 65/4 60/4 84/3.5 83/3 81/2.5 79/2.5 66/4 61/4 60/4

In Scheme 1, the R and CO2R′ groups should be exchanged in the upper amino acid of the structure in the “RCOCH(N1N2) system” (III) (part A) and in product 3 (part C) as shown. In Tables 2 and 3, the groups in column 2 have been corrected. In Table 2, 3k should be isobutyl, and in Table 3, 3u−3z should be isobutyl. The corrected tables are shown. In Scheme 3, eq (9), the dotted bond should be a wedge bond. The corrected scheme is shown.

a

Received: February 3, 2016 Published: February 17, 2016

Reaction conditions: 1 (1 mmol), 2 (1.2 mmol), pyridine (1.5 mmol), selenium dioxide (1.2 mmol), and ACN (3 mL). bIsolated yields. cd-isomer. © 2016 American Chemical Society

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DOI: 10.1021/acs.orglett.6b00353 Org. Lett. 2016, 18, 1217−1218

Organic Letters

Addition/Correction

Scheme 3. Control Experiments

The product configurations for 3i−l,p−z,aa,ac in the Supporting Information are corrected. A corrected version of the Supporting Information is available with this correction.



ASSOCIATED CONTENT

S Supporting Information *

The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.orglett.6b00353. Revised Supporting Information with corrected product configurations for 3i−l,p−z,aa,ac (PDF)

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DOI: 10.1021/acs.orglett.6b00353 Org. Lett. 2016, 18, 1217−1218