Lanthanide(III) catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals: Catalytic asymmetric route to monosaccharides

Koichi Mikam, Masahiro Terada, Takeshi Nakai

Research output: Contribution to journalArticlepeer-review

21 Citations (Scopus)

Abstract

The Pr-, Eu- and Ho(dppm)3 catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals are described, where remarkably high anti-diastereofacial selection is achieved. Thus, the asymmetrc synthesis of 2-deoxy-D-ribonolactone and formal synthesis of 2-amino-2-deoxy-D-pentose by the lanthanide(III) catalyzed aldol reaction with ketene silyl acetals of acetate and a-chloroacetate, respectively are described.

Original languageEnglish
Pages (from-to)993-996
Number of pages4
JournalTetrahedron: Asymmetry
Volume2
Issue number10
DOIs
Publication statusPublished - 1991
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Fingerprint Dive into the research topics of 'Lanthanide(III) catalyzed aldol reactions of glyceraldehyde acetonide with ketene silyl acetals: Catalytic asymmetric route to monosaccharides'. Together they form a unique fingerprint.

Cite this