Enantio- and diastereoselective catalysis of addition reaction of allylic silanes and stannanes to glyoxylates by binaphthol-derived titanium complex

Seiichi Aoki, Koichi Mikami, Masahiro Terada, Takeshi Nakai

Research output: Contribution to journalArticlepeer-review

122 Citations (Scopus)

Abstract

Chiral titanium complex (1), prepared in situ from optically pure binaphthol and diisopropoxytitanium dihalide in the presence of molecular sieves, is shown to catalyze the addition reactions of crotylsilanes and -stannanes to glyoxylates to afford (syn)-α-hydroxy-β-methyl esters in highly scalemic forms with high diastereoselectivity.

Original languageEnglish
Pages (from-to)1783-1792
Number of pages10
JournalTetrahedron
Volume49
Issue number9
DOIs
Publication statusPublished - 1993 Feb 26
Externally publishedYes

Keywords

  • Allylic silane
  • Allylic stannane
  • Asymmetric catalysis
  • Binaphthol-derived titanium dihalide
  • Carbonyl-addition reaction
  • Carbonyl-ene reaction
  • Chiral titanium complex
  • Diastereocontrol
  • Enantiocontrol
  • Glyoxylate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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