Diastereoselective addition reactions of furyl aldehydes using chiral boronates as auxiliary: Application to the enantioselective synthesis of 2,3-disubstituted furyl alcohols

Kin Fai Chan, Henry N.C. Wong

Research output: Journal article publicationJournal articleAcademic researchpeer-review

23 Citations (Scopus)

Abstract

matrix presented The addition reactions of various nucleophiles to a furyl aldehyde bearing a chiral boronate at the C-3 position furnished chromatographically separable diastereomers. The R diastereoselection was more favorable when no additive was added. Surprisingly, when lithium alkoxides were selected as additives, the S diastereoselection is superior instead. Further transformation of C-B bonds to C-C bonds was achieved by using standard Suzuki coupling conditions to give optically active 2,3-disubstituted furyl alcohols.
Original languageEnglish
Pages (from-to)3991-3994
Number of pages4
JournalOrganic Letters
Volume3
Issue number25
DOIs
Publication statusPublished - 13 Dec 2001
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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