A new strategy for the synthesis of alpha-difluoromethyl-substituted alpha-hydroxy and alpha-amino acids

被引：70

作者：

Osipov, SN

Golubev, AS

Sewald, N

Michel, T

Kolomiets, AF

Fokin, AV

Burger, K

机构：

[1] AN NESMEYANOV ORGANOELEMENT CPDS INST, MOSCOW 117813, RUSSIA

[2] UNIV LEIPZIG, INST ORGAN CHEM, D-04103 LEIPZIG, GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 21期

关键词：

D O I：

10.1021/jo9608331

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the preparation of alpha-chlorodifluoromethyl-, alpha-bromodifluoromethyl-, and alpha-difluoromethyl-substituted alpha-hydroxy and alpha-amino acid esters 11, 19-21 is described. The key step of the synthesis is the regioselective alkylation of ketones 5, 7-9 and imines 16-18 with C-nucleophiles. The ketones 7-9 are readily available from 3,3,3-trifluorolactate I by a five-step procedure. Subsequent removal of the protecting groups from 19-21 provides the corresponding : free amino acids 25, 26, 28.

引用

页码：7521 / 7528

页数：8

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