Highly Diastereoselective Vinylogous Mukaiyama Aldol Reaction of Isatins with 2-(Trimethylsilyloxy)furans Catalyzed by Quinine
摘要：
The diastereoselective formation of δ-hydroxyalkyl butenolide oxindoles has been achieved via a vinylogous Mukaiyama aldol reaction. The reaction was performed using various (N-alkyl)isatins 1 with 2-(trimethylsilyloxy)furan 2 catalyzed by quinine in tetrahydrofuran (THF). The reaction proceeds rapidly and affords the corresponding 3-hydroxy-(5-oxo-2,5-dihydrofuran-2-yl)indolin-2-ones in good yields with high diastereoselectivities (anti/syn ratio up to 96:4). [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] GRAPHICAL ABSTRACT
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关键词：
Diastereoselective synthesis 3-hydroxyoxindole isatins quinine vinylogous Mukaiyama aldol reaction
DOI：
10.1080/00397911.2013.837926
被引量：
年份：
2014
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