Enantioselective synthesis of 2-methyl-1,2-syn- and 2-methyl-1,2-anti-3-butenediols via allene hydroboration-aldehyde allylboration reaction sequences

J Am Chem Soc. 2009 Oct 21;131(41):14602-3. doi: 10.1021/ja904599h.

Abstract

The hydroboration of allene 7 with ((d)Ipc)(2)BH at 0 degrees C provides the kinetic allylborane 12Z with >20:1 selectivity. However, when the hydroboration is performed at 85 degrees C, the kinetically formed allylborane isomerizes to give the thermodynamic allylborane 12E with >or=12:1 selectivity. Subsequent treatment of 12Z or 12E with aldehydes at -78 degrees C, followed by oxidative workup, provides the 2-methyl-1,2-diols 8 and 9 in good yield and with 80-92% e.e.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry*
  • Aldehydes / chemistry*
  • Alkadienes / chemistry*
  • Boron / chemistry*
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Alcohols
  • Aldehydes
  • Alkadienes
  • propadiene
  • Boron