Asymmetric Synthesis of β-Amino Acids by Addition of Chiral Enolates to N-Acyloxyiminium Ions and Application for Synthesis of Optically Active 5-Substituted 8-Methylindolizidines

N-Acyloxyiminium species generated from nitrones with acyl halides are highly reactive and can undergo reaction with soft nucleophiles such as enolates. Optically active β-amino acid derivatives can be prepared using chiral enolates bearing chiral auxiliary. The usefulness of the present method is d...

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Bibliographic Details
Published in:Organic letters 1999-07, Vol.1 (1), p.107-110
Main Authors: Kawakami, Toru, Ohtake, Hiroaki, Arakawa, Hiroaki, Okachi, Takahiro, Imada, Yasushi, Murahashi, Shun-Ichi
Format: Article
Language:English
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Summary:N-Acyloxyiminium species generated from nitrones with acyl halides are highly reactive and can undergo reaction with soft nucleophiles such as enolates. Optically active β-amino acid derivatives can be prepared using chiral enolates bearing chiral auxiliary. The usefulness of the present method is demonstrated by the enantioselective synthesis of (5R,8R,8aS)-5-cyano-8-methylindolizidine ((−)-7), which is a common key intermediate for 5-substituted 8-methylindolizidines.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9905755