A practical chiral bicyclic thioglycolate lactam auxiliary for stereoselective quaternary carbon formation

被引：40

作者：

Arpin, A ^{[1
]}

Manthorpe, JM ^{[1
]}

Gleason, JL ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 07期

关键词：

D O I：

10.1021/ol060106k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Chiral bicyclic thioglycolate lactams may be prepared in three steps from inexpensive commercial materials. The resulting lactams may be alkylated three times, twice using basic enolization and once using reductive enolization, to form alpha-quaternary carboxylic acid derivatives in high yield and with high diastereoselectivity. The alkylation products may be cleaved under either acidic or reductive conditions to furnish either carboxylic acids or primary alcohols, respectively.

引用

页码：1359 / 1362

页数：4

共 36 条

[1] Toward the development of a general chiral auxiliary. 9. Highly diastereoselective alkylations and acylations to form tertiary and quaternary centers [J].