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. 2001 Apr 19;3(8):1225-8.
doi: 10.1021/ol0157003.

Stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans

F Cohen  1 , D W MacMillan, L E Overman, A Romero
Affiliations

Stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans

F Cohen et al. Org Lett. .

Abstract

[reaction: see text]. Depending upon the nature of the alkene and allylic substituents, acid-promoted rearrangements of acetals derived from anti allylic diols give 12 or stereoisomeric acyltetrahydrofurans 13. Stereoelectronic effects of the allylic substituents and the extent of bonding in the Prins cyclization transition state are central features of a proposed new model for predicting stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans.

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