A simple enantioselective route toward (R)- and (S)-Rolipram via anhydride desymmetrization

被引：6

作者：

Ivsic, Trpimir ^{[1
]}

Hamersak, Zdenko ^{[1
]}

机构：

[1] Rudjer Boskovic Inst, Dept Organ Chem & Biochem, Zagreb 10002, Croatia

来源：

TETRAHEDRON-ASYMMETRY | 2013年 / 24卷 / 04期

关键词：

QUININE-MEDIATED DESYMMETRIZATION; EFFICIENT ASYMMETRIC-SYNTHESIS; GLUTARIC MESO-ANHYDRIDES; CARBOXYLIC-ACID ESTERS; GAMMA-AMINO ACIDS; PHOSPHODIESTERASE INHIBITORS; CONJUGATE ADDITION; ARYLBORONIC ACIDS; CYCLIC ANHYDRIDE; GABA ANALOGS;

D O I：

10.1016/j.tetasy.2013.01.009

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A highly enantioselective metal-free synthesis of both enantiomers of Rolipram is reported. The key stereoinductive step is a cinchona alkaloid catalyzed opening of a cyclic anhydride prepared from isovanillin, where both enantiomers are available using the same chiral catalyst in two protocols. An extended one-pot Curtius sequence provides the lactam directly from the desymmetrization product after enrichment in high yield and excellent ee. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：217 / 222

页数：6

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