α-Hydroxyalkyl Heterocycles via Chiral Allylic Boronates: Pd-Catalyzed Borylation Leading to a Formal Enantioselective lsomerization of Allylic Ether and Amine

被引：62

作者：

Lessard, Stephanie ^{[1
]}

Peng, Feng ^{[1
]}

Hall, Dennis G. ^{[1
]}

机构：

[1] Univ Alberta, Dept Chem, Edmonton, AB T6G 2G2, Canada

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2009年 / 131卷 / 28期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ASYMMETRIC ISOMERIZATION; 3-COMPONENT; ALLYLAMINES; MIGRATION; COMPLEXES; SEQUENCE; HALIDES; ROUTE; BINAP;

D O I：

10.1021/ja903946f

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) An efficient catalytic enantioselective preparation of synthetically useful pyranyl and piperidinyl allylic boronates was achieved via a palladium-catalyzed borylation/isomerization reaction on the corresponding alkenyl triflates. The influence of the base and solvent was found to be crucial on the regio- and enantioselectivity of this reaction. The overall borylation process constitutes a successful example of formal asymmetric isomerization of allylic ether/amine. The resulting allylic boronate reagents add to various aldehydes in a one-pot process to give synthetically useful alpha-hydroxyalkyl derivatives in high stereoselectivity. © 2009 American Chemical Society.

引用

页码：9612 / 9613

页数：2

共 18 条

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