Catalytic Asymmetric Glyoxylate–Ene Reaction: A Practical Access to α-Hydroxy Esters in High Enantiomeric Purities

Koichi Mikami, Masahiro Terada, Takeshi Nakai

Research output: Contribution to journalArticlepeer-review

359 Citations (Scopus)

Abstract

An efficient asymmetric catalysis is developed for the glyoxylate–ene reaction to afford the α-hydroxy esters of biological and synthetic importance. The key to the success is the use of the chiral titanium complex prepared in situ from (i-PrO)2TiX2 (X = Cl or Br) and the (R)- or (S)-binaphthol in the presence of molecular sieves (MS 4A). The presence of the molecular sieves (zeolite) is clarified to facilitate the alkoxy-ligand exchange reaction. Thus, the use of MS is shown to be essential for the in situ preparation step of the chiral catalyst and not for the ene reaction step. The present catalytic process is applicable to various 1, 1-disubstituted olefins by the judicious choice of the dichloro or dibromo catalyst.

Original languageEnglish
Pages (from-to)3949-3954
Number of pages6
JournalJournal of the American Chemical Society
Volume112
Issue number10
DOIs
Publication statusPublished - 1990 Jan 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Catalytic Asymmetric Glyoxylate–Ene Reaction: A Practical Access to α-Hydroxy Esters in High Enantiomeric Purities'. Together they form a unique fingerprint.

Cite this