An Efficient Petasis Boronic-Mannich Reaction of Chiral Lactol Derivatives Prepared from d -Araboascorbic Acid

Hiroki Mandai, Hiroshi Yamada, Keita Shimowaki, Koichi Mitsudo, Seiji Suga

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Optically active polyhydroxy trans-1,2-amino alcohols were efficiently synthesized in good to excellent yields by the Petasis boronic-Mannich reaction of an amine, an organoboronic acid, and a chiral lactol, which was prepared from d-araboascorbic acid or its diastereomer. Further transformations of the resulting Petasis products were investigated in detail to obtain chiral building blocks containing three continuous stereogenic centers.

Original languageEnglish
Article numberss-2014-c0373-op
Pages (from-to)2672-2681
Number of pages10
JournalSynthesis (Germany)
Volume46
Issue number19
DOIs
Publication statusPublished - Oct 1 2014

Keywords

  • asymmetric synthesis
  • chiral pool
  • coupling
  • diastereoselectivity
  • domino reaction
  • lactones

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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