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Synthesis 2009(10): 1694-1702  
DOI: 10.1055/s-0028-1088044
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Portion Synthesis of 2-Acetoxy Carbonyl Compounds from Aldehydes by Using an Acetylated Masked Acyl Cyanide

Hisao Nemoto*, Tomoyuki Kawamura, Kyoko Kitasaki, Kenji Yatsuzuka, Masaki Kamiya, Yasuko Yoshioka
Division of Pharmaceutical Chemistry, Institute of Health Biosciences, Graduate School, The University of Tokushima, 1-78 Sho-machi, Tokushima 770-8505, Japan
Fax: +81(88)6337284; e-Mail: nem@ph.tokushima-u.ac.jp;
Further Information

Publication History

Received 2 December 2008
Publication Date:
25 March 2009 (online)

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Abstract

α-Acetoxy esters or amides were synthesized directly and in one portion from aldehydes and alcohols or amines by one-carbon homologation using a masked acyl cyanide reagent bearing an acetyl group.

Key words

masked acyl cyanide - one-portion synthesis - 2-acetoxy esters - 2-acetoxy amides - umpolung

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6

General structure 1 is from reference 3i.