Stereoselection in the prins-pinacol synthesis of acyltetrahydrofurans

Frederick Cohen, David W.C. MacMillan, Larry E. Overman, Alex Romero

Research output: Contribution to journalArticle

40 Scopus citations

Abstract

Matrix presented 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.

Original languageEnglish (US)
Pages (from-to)1225-1228
Number of pages4
JournalOrganic letters
Volume3
Issue number8
DOIs
StatePublished - Apr 19 2001

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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