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Radical reactions on enol-esters: facile synthesis of 3-ulosonic acid derivatives and chiral spiroacetals

✍ Scribed by G.V.M. Sharma; Rakesh; A.Subhash Chander; V.Goverdhan Reddy; M.H.V.Ramana Rao; A.C. Kunwar

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 617 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00448-8

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✦ Synopsis

A two-step approach to 3-ulosonic acid derivatives and chiral spiroacetals from enol-esters is presented. The strategy involves 1,4-addition of a variety of alcohols onto enol-esters in the presence of NBS to give a-bromoacetals, which undergo a regio-and stereoselective radical cyclisation to give the highly functionalised chiral spiroacetals, while debromination gives 3-ulosonic acid derivatives.

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