Journal
ORGANIC LETTERS
Volume 3, Issue 8, Pages 1225-1228Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol0157003
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- NINDS NIH HHS [NS-12389] Funding Source: Medline
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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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