Asymmetric Synthesis of α-Chloro-β-amino-N-sulfinyl Imidates as Chiral Building Blocks

被引：44
|
作者：
Colpaert, Filip [1 ]
Mangelinckx, Sven [1 ]
De Brabandere, Stijn [1 ]
De Kimpe, Norbert [1 ]
机构：
[1] Univ Ghent, Dept Sustainable Organ Chem & Technol, Fac Biosci Engn, B-9000 Ghent, Belgium
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 76卷 / 07期
基金：
比利时弗兰德研究基金会;
关键词：
MANNICH-TYPE REACTIONS; ACID-DERIVATIVES; NITRILE BIOTRANSFORMATIONS; STEREOSELECTIVE-SYNTHESIS; AQUEOUS-SOLUTION; SULFINIMINES; EFFICIENT; DESIGN; IMINES; REACTIVITY;
D O I：
10.1021/jo200082w
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New chiral alpha-chloro-beta-amino-N-sulfinyl imidates were synthesized in high yield and excellent diastereomeric excess via highly anti-selective Mannich-type reactions of (R-S)-methyl N-tert-butanesulfinyl-2-chloroethanimidate with aromatic aldimines. The alpha-chloro-beta-amino-N-sulfinylimidates proved to be excellent building blocks for the asymmetric synthesis of beta-amino-alpha-chloro amides and esters, aziridine-2-carboxylic amides and esters, trans-2-aryl-3-chloroazetidines, and methyl 4-phenyloxazolidin-2-one-5-carboxylate. The obtained absolute anti-diastereoselectivity is the opposite of the stereochemical outcome observed for alpha-methyl-substituted imidates.
引用
收藏
页码：2204 / 2213
页数：10
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