Organocatalytic asymmetric domino Knoevenagel/Diels-Alder reactions: A bioorganic approach to the diastereospecific and enantioselective construction of highly substituted spiro[5,5]undecane-1,5,9-triones

被引：332

作者：

Ramachary, DB ^{[1
]}

Chowdari, NS ^{[1
]}

Barbas, CF ^{[1
]}

机构：

[1] Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2003年 / 42卷 / 35期

关键词：

amino acids; asymmetric catalysis; cycloaddition; domino reactions; enantioselectivity;

D O I：

10.1002/anie.200351916

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A practical and environmentally friendly organocatalytic process for the synthesis of optically active highly substituted spiro[5,5]undecane-1,5,9-triones was achieved through the reaction of an aldehyde, an enone, and Meldrum's acid in the presence of a catalytic amount of chiral amino acid (see scheme). The Diels-Alder products were obtained as single diastereomers in excellent yields and enantiomeric excesses.

引用

页码：4233 / 4237

页数：5

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