Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes: synthesis of a fragment of (+)-vibsanin A

Akihiro Sakama, Yoshiyasu Nishimura, Yuko Motohashi, Keisuke Yoshida, Ken ichi Takao

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

Stereoselective construction of all-carbon quaternary stereocenters by allylboration of chiral aldehydes is described. Sugar-derived aldehydes were allylated with geranylboronate or nerylboronate to provide γ-adducts possessing quaternary stereocenters with high diastereoselectivity. The reaction was applied to the synthesis of a fragment of (+)-vibsanin A.

Original languageEnglish
Pages (from-to)5465-5471
Number of pages7
JournalTetrahedron
Volume72
Issue number35
DOIs
Publication statusPublished - 2016

Keywords

  • Allylation
  • Boronates
  • Carbohydrates
  • Diastereoselectivity
  • Quaternary stereocenter

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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