Acyclic stereocontrol in the Ireland-Claisen rearrangement of α-branched esters

被引：79
|
作者：
Qin, Ying-Chuan [1 ]
Stivala, Craig. E. [1 ]
Zakarian, Armen [1 ]
机构：
[1] Florida State Univ, Dept Chem & Biochem, Tallahassee, FL 32306 USA
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2007年 / 46卷 / 39期
关键词：
chiral amines; diastereoselectivity; enolization; Ireland-Claisen rearrangement; synthetic methods;
D O I：
10.1002/anie.200702142
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) To overcome the limitation of the poor diastereoselectivity of the title reaction with α-branched esters, chiral amides were used to generate the enolate intermediates diastereoselectively. The desired rearrangement then took place with efficient transfer of chirality to give densely functionalized products with at least one quaternary stereocenter (see scheme; PMB, TBS, and TBDPS are protecting groups). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：7466 / 7469
页数：4
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