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Radical mediated stereoselective synthesis of chiral spiroacetals from enol-esters

✍ Scribed by G.V.M Sharma; A.Subash Chander; V Goverdhan Reddy; K Krishnudu; M.H.V Ramana Rao; A.C Kunwar

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
118 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

Stereoselective synthesis of chiral spiroacetals starting from enol-ester 1, derived from D-manno lactone, is described. The strategy involves 1,4-addition of a variety of alcohols to 1 in the presence of NBS to give Ξ±bromo acetals, which undergo a regio-and stereoselective radical cyclisation to give highly functionalised chiral spiroacetals.

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