Rhodium(II)-Catalyzed Reaction of Iodonium Ylides with Conjugated Compounds: Efficient Synthesis of Dihydrofurans, Oxazoles, and Dihydrooxepines

Yong Rok Lee; Sang Heum Yoon; Youngwan Seo; Bong Sik Kim

doi:10.1055/s-2004-831257

PAPER

Rhodium(II)-Catalyzed Reaction of Iodonium Ylides with Conjugated Compounds: Efficient Synthesis of Dihydrofurans, Oxazoles, and Dihydrooxepines

Yong Rok Lee*^a, Sang Heum Yoon^a, Youngwan Seo^b, Bong Sik Kim^a
^a School of Chemical Engineering and Technology, College of Engineering, Yeungnam University, Kyongsan 712-749, Korea
Fax: +82(53)8104631; e-Mail: yrlee@yu.ac.kr;
^b Division of Ocean Science, Korea Maritime University, Busan 606-791, Korea

Abstract

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Abstract

The rhodium(II)-catalyzed reaction of iodonium ylides with a variety of conjugated compounds has been examined. With α,β-unsaturated esters and α,β-unsaturated ketones, dihydrofurans were produced in moderate yields. Reactions with acrylonitriles yield oxazoles and dihydrofurans in moderate yields, whereas reactions with 1,3-butadienes result in dihydrofurans and dihydrooxepines in good yields, respectively. The mechanistic pathway for the formation of these products has been described in terms of a cyclopropane intermediate or a 1,3-dipolar cycloaddition mechanism.

Key words

iodonium ylides - rhodium(II)-catalyzed reaction - dihydrofurans - oxazoles - dihydrooxepines

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