Dess-Martin periodinane promoted oxidative coupling of Baylis-Hillman adducts with silyl enol ethers: a novel synthesis of cis-fused dihydropyrans

Yadav, J. S. ; Subba Reddy, B. V. ; Mandal, S. S. ; Basak, A. K. ; Madavi, C. ; Kunwar, A. C. (2008) Dess-Martin periodinane promoted oxidative coupling of Baylis-Hillman adducts with silyl enol ethers: a novel synthesis of cis-fused dihydropyrans Synlett, 2008 (8). pp. 1175-1178. ISSN 0936-5214

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Official URL: https://www.thieme-connect.com/ejournals/abstract/...

Related URL: http://dx.doi.org/10.1055/s-2008-1072730

Abstract

Baylis-Hillman adducts undergo smooth oxidative Mukaiyama-Michael addition and a subsequent cyclization with silyl enol ethers in the presence of Dess-Martin periodinane (DMP) and pyridine under mild reaction conditions to afford a new class of dihydropyran derivatives in good yields with high diastereoselectivity. This is the first report on the preparation of cis-fused dihydropyrans from Baylis-Hillman adducts and silyl enol ethers.

Item Type:Article
Source:Copyright of this article belongs to Thieme Medical Publishers.
Keywords:Baylis-Hillman Adducts; Hypervalent Iodine; Enol Ethers; Oxidative Mukaiyama-Michael Addition
ID Code:63064
Deposited On:28 Sep 2011 03:37
Last Modified:28 Sep 2011 03:37

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