Stereocontrolled route to vicinal diamines by [3.3] sigmatropic rearrangement of allyl cyanate: asymmetric synthesis of anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids

Org Lett. 2006 Dec 7;8(25):5737-40. doi: 10.1021/ol0621102.

Abstract

A stereocontrolled route via allyl 1,2-diols to vicinal diamines based on the [3.3] sigmatropic rearrangement of allyl cyanate has been developed. Our approach consists of two consecutive steps: stereoselective construction of allyl anti- and syn-1,2-diols followed by [1,3]-chirality transfer by sigmatropic rearrangement, which allow an access to anti-(2R,3R)- and syn-(2R,3S)-2,3-diaminobutanoic acids. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetaldehyde / chemistry
  • Allyl Compounds / chemistry*
  • Aminobutyrates / chemical synthesis*
  • Diamines / chemical synthesis*
  • Indicators and Reagents
  • Isocyanates / chemistry*
  • Ketones / chemistry
  • Molecular Conformation
  • Organophosphonates / chemistry
  • Reducing Agents
  • Stereoisomerism

Substances

  • Allyl Compounds
  • Aminobutyrates
  • Diamines
  • Indicators and Reagents
  • Isocyanates
  • Ketones
  • Organophosphonates
  • Reducing Agents
  • allyl isocyanate
  • 2,3-diaminobutanoic acid
  • Acetaldehyde