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Synthesis 2008(20): 3229-3236  
DOI: 10.1055/s-0028-1083153
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New One-Pot Synthetic Method for Selenium-Containing Medium-Sized α,β-Unsaturated Cyclic Ketones [¹]

Haruki Sashida*, Akemi Nakayama, Mamoru Kaname
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanagawa-machi, Kanazawa 920-1181, Japan
Fax: +81(76)2292781; e-Mail: h-sashida@hokuriku-u.ac.jp;
Further Information

Publication History

Received 12 June 2008
Publication Date:
25 September 2008 (online)

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Abstract

The reaction of tetrahydroselenopyran-2-one (7) with ethynyllithiums 20a-h, followed by treatment with aqueous 5% H2SO4 successfully led to a two-carbon ring expansion to give the 2-substituted 5,6,7,8-tetrahydroselenocin-4-ones 21a-h in 43-95% yields. Seven- to nine-membered γ-selena-α,β-unsaturated cyclic ketones 22-26 and a 5,6,7,8-tetrahydrotellurocin-4-one 27 were also prepared from the corresponding selenolactones or tellurolactone in a one-pot reaction.

Key words

selenolactone - ethynyllithium - ring expansion - selenium - selenoketone

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