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
1217
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.
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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.orglett.6b00353. Revised Supporting Information with corrected product configurations for 3i−l,p−z,aa,ac (PDF)
1218
DOI: 10.1021/acs.orglett.6b00353 Org. Lett. 2016, 18, 1217−1218
