Bridgehead enolates: Substitution and asymmetric desymmetrization of small bridged carbonyl compounds by lithium amide bases

被引：20

作者：

Giblin, GMP

Kirk, DT

Mitchell, L

Simpkins, NS

机构：

[1] Univ Nottingham, Sch Chem, Nottingham NG7 2RD, England

[2] GlaxoSmithKline, Dept Med Chem, Neurol CEDD, Welwyn Garden City AL6 9AR, Herts, England

来源：

ORGANIC LETTERS | 2003年 / 5卷 / 10期

关键词：

D O I：

10.1021/ol034348l

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Contrary to expectations, a number of bridged carbonyl compounds undergo facile bridgehead metalation with lithium amide bases. Diketone, lactone, lactam, and imide functions are all demonstrated to participate in this type of "bridgehead enolate" chemistry, leading to a range of substituted products. Meso compounds can also be desymmetrized in very high ee by asymmetric bridgehead metalation.

引用

页码：1673 / 1675

页数：3

共 22 条

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