Generation of stereochemically defined tetrasubstituted enolborinates by 1,4-hydroboration of α,β-unsaturated morpholine carboxamides with (diisopinocampheyl)borane

Angew Chem Int Ed Engl. 2013 Dec 2;52(49):12888-12891. doi: 10.1002/anie.201307302. Epub 2013 Oct 15.

Abstract

On all fours: The title reaction with (Ipc)2 BH provides tetrasubstituted enolborinates which undergo aldol reactions with aldehydes to form products with all-carbon quaternary centers with exceptional diastereo- and enantioselectivity. A change to the substitution pattern of the starting amide leads to either diastereomer of the α-methyl-α-ethyl-β-hydroxy carboxamide (1 or 2).

Keywords: amides; boron; enantioselectivity; enols; synthetic methods.

Publication types

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

MeSH terms

  • Aldehydes / chemistry
  • Amides / chemistry*
  • Boranes / chemistry*
  • Boron Compounds / chemical synthesis*
  • Catalysis
  • Morpholines / chemistry*
  • Stereoisomerism

Substances

  • (diisopinocampheyl)borane
  • Aldehydes
  • Amides
  • Boranes
  • Boron Compounds
  • Morpholines
  • morpholine