Stereoselective synthesis of gamma-substituted (Z)-allylic boranes via kinetically controlled hydroboration of allenes with 10-TMS-9-borabicyclo[3.3.2]decane

J Am Chem Soc. 2009 Oct 14;131(40):14174-5. doi: 10.1021/ja905494c.

Abstract

Kinetically controlled hydroboration of allenes 8 and 14a-d with the readily accessible Soderquist borane 7, which is generated in situ from borohydride 6, constitutes a convenient and preparatively useful method for synthesis of (Z)-gamma-(substituted)allylboranes 9 and 15a-d. These allylboranes undergo highly diastereo- (> or = 90: 10) and enantioselective (typically 89-96% e.e.) allylboration reactions with representative aldehydes to give syn-beta-functionalized homoallylic alcohols.

Publication types

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

MeSH terms

  • Alkadienes / chemistry*
  • Alkanes / chemistry*
  • Allyl Compounds / chemical synthesis*
  • Boranes / chemical synthesis*
  • Bridged Bicyclo Compounds / chemistry*
  • Kinetics
  • Stereoisomerism

Substances

  • Alkadienes
  • Alkanes
  • Allyl Compounds
  • Boranes
  • Bridged Bicyclo Compounds
  • propadiene
  • decane