Migratory Dynamic Kinetic Resolution of Carbocyclic Allylic Alcohols

被引：13

作者：

Sapu, Chicco Manzuna ^{[1
]}

Gorbe, Tamas ^{[2
]}

Lihammar, Richard ^{[2
]}

Backvall, Jan-E. ^{[2
]}

Deska, Jan ^{[1
]}

机构：

[1] Univ Cologne, Dept Chem, D-50939 Cologne, Germany

[2] Stockholms Univ, Dept Organ Chem, S-10691 Stockholm, Sweden

来源：

ORGANIC LETTERS | 2014年 / 16卷 / 22期

基金：

瑞典研究理事会;

关键词：

TERTIARY ALCOHOLS; CATALYSIS; DESYMMETRIZATION; REARRANGEMENT;

D O I：

10.1021/ol502979g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel migratory dynamic kinetic resolution based on the interplay between an enzyme acylation catalyst and a heterogeneous Bronsted acid as an isomerization/racemization catalyst gives rise to carbocyclic allylic esters with excellent stereoselectivity from readily available tertiary carbinols. An easy-to-use teabag setup combining resin-bound catalysts, a biphasic isooctanewater solvent system, and a highly lipophilic acyl donor efficiently suppresses side reactions and allows for the preparation of functionalized carbocyclic building blocks in high yields and optical purity.

引用

页码：5952 / 5955

页数：4

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