C(2)-symmetric Sc(III)-complexes as chiral Lewis acids. Catalytic enantioselective aldol additions to glyoxylate esters

Org Lett. 2002 Oct 3;4(20):3375-8. doi: 10.1021/ol026488l.

Abstract

Cationic Lewis acid complexes [Sc(pyridyl-bis(oxazolinyl)](Cl(2))SbF(6) 1a and 1b catalyze aldol reactions with ethyl glyoxylate with enantioselectivities ranging from 90 to 99% ee and syn reaction diastereoselections ranging from 90:10 to 95:5. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acids, Heterocyclic / chemistry*
  • Aldehydes / chemistry*
  • Catalysis
  • Cations / chemistry
  • Esters / chemistry*
  • Glyoxylates / chemistry*
  • Models, Molecular
  • Molecular Conformation
  • Molecular Structure
  • Scandium / chemistry*
  • Stereoisomerism

Substances

  • Acids, Heterocyclic
  • Aldehydes
  • Cations
  • Esters
  • Glyoxylates
  • 3-hydroxybutanal
  • Scandium