Asymmetric catalytic Strecker reaction of N-phosphonyl imines with Et2AlCN using amino alcohols and BINOLs as catalysts

Chem Commun (Camb). 2010 Jun 28;46(24):4330-2. doi: 10.1039/c0cc00287a. Epub 2010 May 12.

Abstract

The asymmetric catalytic Strecker reaction of achiral N-phosphonyl imines with Et(2)AlCN has been established. Both free amino alcohols and BINOLs have been proven to be effective catalysts to afford excellent enantioselectivities and yields. The N-phosphonyl group can be readily cleaved under mild conditions and enable purification of crude products by simple washing with hexane. The cleaved N,N-dialkyl diamine auxiliary can be recovered quantitatively via n-BuOH extraction. The scope for both N-phosphonyl imines and catalysts was vastly studied for this new catalytic system.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aluminum / chemistry*
  • Amino Alcohols / chemistry*
  • Catalysis
  • Imines / chemistry*
  • Naphthols / chemistry*
  • Organometallic Compounds / chemistry*
  • Stereoisomerism

Substances

  • Amino Alcohols
  • BINOL, naphthol
  • Imines
  • Naphthols
  • Organometallic Compounds
  • Aluminum