Highly catalytic asymmetric addition of deactivated alkyl grignard reagents to aldehydes

Org Lett. 2009 Dec 17;11(24):5578-81. doi: 10.1021/ol9020942.

Abstract

Generally used and highly reactive RMgBr reagents were effectively deactivated by bis[2-(N,N-dimethylamino)ethyl] ether and then were employed in the highly enantioselective addition of Grignard reagents to aldehydes. The reaction was catalyzed by the complex of commercially available (S)-BINOL and Ti(O(i-)Pr)(4) under mild conditions. Compared with the other observed Grignard reagents, alkyl Grignard reagents showed higher enantioselectivity and they achieved >99% ee.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Ethyl Ethers / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Naphthols / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • BINOL, naphthol
  • Ethyl Ethers
  • Indicators and Reagents
  • Naphthols
  • bis(2-(dimethylamino)ethyl) ether