Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of α-Halo Thioesters and Enolizable Aldehydes

被引：21

作者：

Sauer, Scott J. ^{[1
]}

Garnsey, Michelle R. ^{[1
]}

Coltart, Don M. ^{[1
]}

机构：

[1] Duke Univ, Dept Chem, Durham, NC 27708 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 40期

基金：

美国国家科学基金会;

关键词：

POLYKETIDE SYNTHASES; KETONES; TRIETHYLAMINE;

D O I：

10.1021/ja1057407

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct addition of enolizable aldehydes and alpha-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the unusual feature of giving high syn-selectivity, which is the opposite of that produced for (thio)esters under conventional conditions. Moreover, excellent diastereoselectivity results when a chiral nonracemic alpha-hydroxy aldehyde derivative is used.

引用

页码：13997 / 13999

页数：3

共 37 条

[1] Alcaide B, 2002, EUR J ORG CHEM, V2002, P1595
[2] Towards organocatalytic polyketide synthases with diverse electrophile scope: Trifluoroethyl thioesters as nucleophiles in organocatalytic Michael reactions and beyond
Alonso, Diego A.
Kitagaki, Shinji
Utsumi, Naoto
Barbas, Carlos F., III
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (24) : 4588 - 4591
[3] Carreira E.M., 1999, Comprehensive Assymetric Catalysis, V3, P997
[4] Ni(II) bis(oxazoline)-catalyzed enantioselective syn aldol reactions of N-propionylthiazolidinethiones in the presence of silyl triflates
Evans, DA
Downey, CW
Hubbs, JL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (29) : 8706 - 8707
[5] Magnesium halide-catalyzed anti-aldol reactions of chiral N-acylthiazolidinethiones
Evans, DA
Downey, CW
Shaw, JT
Tedrow, JS
[J]. ORGANIC LETTERS, 2002, 4 (07) : 1127 - 1130
[6] Diastereoselective magnesium halide-catalyzed anti-aldol reactions of chiral N-acyloxazolidinones
Evans, DA
Tedrow, JS
Shaw, JT
Downey, CW
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (03) : 392 - 393
[7] Phosphine/Lewis acid mediated reformatsky-type reaction of α-bromoketone or -thioester derivatives
Hashimoto, Y
Kikuchi, S
[J]. CHEMISTRY LETTERS, 2002, (02) : 126 - 127
[8] BETA-HYDROXY ESTERS FROM KETONES AND ESTERS
HAUSER, CR
PUTERBAUGH, WH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (06) : 2972 - 2972
[9] Heathcock C.H., 1992, Modern Synthetic Methods, V6, P1
[10] Heathcock C.H., 1991, COMPREHENSIVE ORGANI, V2, P133, DOI [10.1016/B978-0-08-052349-1.00027-5, DOI 10.1016/B978-0-08-052349-1.00027-5]

← 1 2 3 4 →