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
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
收藏
页码:5952 / 5955
页数:4
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