Convenient asymmetric synthesis off β-substituted α,α-difluoro-β-amino acids via Reformatsky reaction between Davis' N-sulfinylimines and ethyl bromodifluoroacetate

被引：84

作者：

Sorochinsky, A ^{[1
]}

Voloshin, N

Markovsky, A

Belik, M

Yasuda, N

Uekusa, H

Ono, T

Berbasov, DO

Soloshonok, VA

机构：

[1] Ukrainian Acad Sci, Inst Bioorgan Chem & Petrochem, UA-253660 Kiev, Ukraine

[2] Tokyo Inst Technol, Dept Chem & Mat Sci, Meguro Ku, Tokyo 1528551, Japan

[3] Natl Inst Adv Ind Sci & Technol, Mol Struct Design Grp, Inst Struct & Engn Mat, Moriyama Ku, Nagoya, Aichi 4638560, Japan

[4] Univ Oklahoma, Dept Chem & Biochem, Norman, OK 73019 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 19期

关键词：

D O I：

10.1021/jo030082k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enantiopure Davis' N-sulfinylimines were found to be efficient as chiral imine equivalents in the high-temperature Reformatsky-type additions with BrZnCF2COOEt affording an efficient approach to the enantiomerically pure alpha,alpha-difluoro-beta-amino acids. High chemical and stereochemical yields (drs > 9:1, and as high as 99:1) render this method immediately useful for preparing the target amino acids.

引用

页码：7448 / 7454

页数：7

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