Rapid generation of molecular complexity:: Synthesis of α-hydroxyallenes using functionalized Grignard reagents

被引：18

作者：

Deutsch, Carl ^{[1
]}

Hoffman-Roeder, Anja ^{[1
]}

Domke, Axel ^{[1
]}

Krause, Norbert ^{[1
]}

机构：

[1] Univ Dortmund, D-44227 Dortmund, Germany

来源：

SYNLETT | 2007年 / 05期

关键词：

allenes; chirality transfer; functionalized Grignard reagents; organocopper reagents; S(N)2 ' substitution;

D O I：

10.1055/s-2007-970768

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of functionalized aryl-Grignard reagents in the copper-mediated S(N)2' substitution of propargylic oxiranes leads to structurally complex alpha-hydroxyallenes, usually with high yield and diastereoselectivity. Further transformations, such as gold-catalyzed cycloisomerization to 2,5-dihydrofurans and palladium-catalyzed coupling reactions, demonstrate the high potential of these compounds for the rapid generation of molecular complexity.

引用

页码：737 / 740

页数：4

共 42 条

[1] DIASTEREOSELECTIVE SYN OR ANTI OPENING OF PROPARGYLIC EPOXIDES - SYNTHESIS OF ALPHA-ALLENIC ALCOHOLS [J].