Copper catalyzed asymmetric synthesis of chiral allylic esters

被引：80

作者：

Geurts, Koen ^{[1
]}

Fletcher, Stephen P. ^{[1
]}

Feringa, Ben L. ^{[1
]}

机构：

[1] Univ Groningen, Dept Organ Chem & Mol Inorgan Chem, Stratingh Inst, NL-9747 AG Groningen, Netherlands

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2006年 / 128卷 / 49期

关键词：

D O I：

10.1021/ja065780b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The complex derived from Taniaphos ligand 4 and CuBr•Me2S catalyzes the asymmetric addition of Grignard reagents to 3-bromopropenyl esters 1 to provide allylic esters 2 in high yields and high chemio-, regio-, and enantioselectivities. The work demonstrates that allylic asymmetric alkylation (AAA) can be done on substrates bearing a heteroatom at the γ-position. The method is a practical route to chiral, nonracemic allylic alcohols. The use of functionalized substrates 1 or Grignard reagents leads to more complex products 2, which can be further manipulated as demonstrated in conversion to (S)-5-ethyl-2(5H)-furanone 6 and (S)-benzoic acid-cyclopent-2-enyl ester 7. Copyright © 2006 American Chemical Society.

引用

页码：15572 / 15573

页数：2

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