An Approach Toward Oxidopyrylium Ylides Using Rh(II)-Catalyzed Cyclization Chemistry

• Type of Material: Article
• Authors: Albert Padwa, Emory University; Jutatip Boonsombat, Emory University; Paitoon Rashatasakhon, Chulalongkorn University
• Language: English
• Date: 2007-08-20
• Publisher: Elsevier
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © 2007 Elsevier Ltd. All rights reserved.
• License: Creative Commons Attribution-NonCommerical-NoDerivs 3.0 Unported
• Final Published Version (URL): http://dx.doi.org/10.1016/j.tetlet.2007.06.118
• Title of Journal or Parent Work: Tetrahedron Letters
• ISSN: 0040-4039
• Volume: 48
• Issue: 34
• Start Page: 5938
• End Page: 5941
• Grant/Funding Information: We appreciate the financial support provided by the National Institutes of Health (GM 059384) and the National Science Foundation (Grant CHE-0450779).
• Research Categories: Chemistry, General

Abstract

The Rh(II)-catalyzed reaction of the E-isomer of 2-diazo-3,6-dioxo-6-phenyl-hex-enoic acid methyl ester was carried out in the presence of various carbonyl compounds and was found to give 1,3-dioxoles in moderate to good yield. In an attempt to prepare the starting -diazo substrate, an unexpected pseudo-dimerization reaction was encountered when 5-phenyl-furan-2,3-dione was heated in the presence of sodium methoxide.