Alkynoate Synthesis via Vinylogous Reactivity of Rh(II) Carbenoids

• Type of Material: Article
• Authors: Damien Valette, Emory University; Yajing Lian, Emory University; John P. Haydek, Emory University; Kenneth I. Hardcastle, Emory University; Huw Davies, Emory University
• Language: English
• Date: 2012-08-20
• Publisher: Wiley-VCH Verlag
• Publication Version: Author Accepted Manuscript (After Peer Review)
• Copyright Statement: © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
• Final Published Version (URL): http://onlinelibrary.wiley.com/doi/10.1002/anie.201204047/abstract
• Title of Journal or Parent Work: Angewandte Chemie
• ISSN: 0044-8249
• Volume: 51
• Issue: 34
• Start Page: 8636
• End Page: 8639
• Grant/Funding Information: This research was supported by the National Institutes of Health (GM099142).
• Keywords: 2-alkynoate; carbenoids; rhodium; siloxy-vinyldiazo
• Research Categories: Chemistry, General

Abstract

A new rhodium carbenoid approach to access alkynoates has been developed. This transformation combines the addition of enol ethers at the vinylogous position of β-siloxy-substituted vinyldiazo derivatives and an unprecedented siloxy group migration to yield the products as single diastereomers.