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：334
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.
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收藏
页码：4233 / 4237
页数：5
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