(R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE - A VERSATILE CHIRAL DIENOPHILE FROM (S)-MALIC ACID

被引:60
作者
KOOT, WJ [1 ]
HIEMSTRA, H [1 ]
SPECKAMP, WN [1 ]
机构
[1] UNIV AMSTERDAM,DEPT ORGAN CHEM,NIEUWE ACHTERGRACHT 129,1018 WS AMSTERDAM,NETHERLANDS
关键词
D O I
10.1021/jo00030a002
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title compound, readily prepared from (S)-malic acid, reacts as a Diels-Alder dienophile with several 1,3-dienes with excellent regio- and stereoselectivity without loss of enantiomeric purity. The synthesis of an enantiomerically pure intermediate in a projected synthesis of gelsemine is detailed.
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页码:1059 / 1061
页数:3
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