First highly diastereoselective synthesis of syn α-methyl β-fluoroalkyl β-amino esters

被引：48

作者：

Fustero, S ^{[1
]}

Pina, B ^{[1
]}

de la Torre, MG ^{[1
]}

Navarro, A ^{[1
]}

de Arellano, CR ^{[1
]}

Simón, A ^{[1
]}

机构：

[1] Univ Valencia, Fac Farm, Dept Quim Organ, Valencia 46100, Spain

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 07期

关键词：

D O I：

10.1021/ol990774o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] A new two-step approach for the diastereoselective synthesis of the syn alpha-methyl beta-fluoroalkyl beta-amino esters 4 has been developed. This approach is based on the chemical reduction of the fluorinated beta-enamino esters 3, which have been previously obtained from imidoyl chlorides 1 and lithium ester enolates, with Znl(2)/NaBH4 as the reducing agent. The process takes place with high syn diastereoselectivity and good to excellent yields. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction.

引用

页码：977 / 980

页数：4

共 41 条

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