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

被引：38

作者：

Boeckman, RK ^{[1
]}

Boehmler, DJ ^{[1
]}

Musselman, RA ^{[1
]}

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 23期

关键词：

D O I：

10.1021/ol016738i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Enolates of a new camphor-derived lactam auxiliary are shown to monoalkylate with very high diastereoselectivity. A second alkylation occurs with reactive alkylating agents to afford quaternary centers also with high diastereoselectivity, In accord with a proposed model for diastereoselection, lithium and sodium enolates provide products with an opposite sense of asymmetric induction.

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页码：3777 / 3780

页数：4

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