Stereoselective Aldol Reaction of Glutarimides Using Pseudo C 2 Symmetry

The boron aldol reaction of β-substituted glutaric imides bearing an oxazolidinone-based auxiliary proceeds with excellent diastereoselectivity; switching the tertiary amine employed between i-Pr2EtN or Et3N affords enantiomeric lactone product.

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Bibliographic Details
Published in:Organic letters 2010-01, Vol.12 (2), p.268-271
Main Authors: Watanabe, Yohsuke, Yamazaki, Takashi, Kubota, Toshio
Format: Article
Language:English
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Description
Summary:The boron aldol reaction of β-substituted glutaric imides bearing an oxazolidinone-based auxiliary proceeds with excellent diastereoselectivity; switching the tertiary amine employed between i-Pr2EtN or Et3N affords enantiomeric lactone product.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902592t