Stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans

F Cohen; D W MacMillan; L E Overman; A Romero

doi:10.1021/ol0157003

Stereoselection in the Prins-pinacol synthesis of acyltetrahydrofurans

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

Authors

F Cohen¹, D W MacMillan, L E Overman, A Romero

Affiliation

¹ Department of Chemistry, 516 Rowland Hall, University of California, Irvine, California 92697-2025, USA.

PMID: 11348200
DOI: 10.1021/ol0157003

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

MeSH terms

Chemistry, Organic / methods
Furans / chemical synthesis*
Models, Chemical
Time Factors

Substances

Furans
tetrahydrofuran

Grants and funding

NS-12389/NS/NINDS NIH HHS/United States