Diastereoselective synthesis of useful building blocks by crotylation of beta-branched alpha-methylaldehydes with potassium crotyltrifluoroborates

J Org Chem. 2008 Aug 15;73(16):6292-8. doi: 10.1021/jo801106b. Epub 2008 Jul 16.

Abstract

The diastereoselective construction of stereotriads having consecutive methyl, hydroxy, and methyl substituents was realized by the substrate-controlled crotylation of beta-branched alpha-methylaldehydes with potassium crotyltrifluoroborates. Especially, crotylation of 2-(1,3-dithian-2-yl)propanal with potassium ( E)-crotyltrifluoroborate afforded, in good yield and with excellent diastereoselectivity, a useful building block that has different and potential functional groups on both ends.

MeSH terms

  • Aldehydes / chemistry*
  • Borates / chemistry*
  • Butanes / chemistry
  • Stereoisomerism

Substances

  • Aldehydes
  • Borates
  • Butanes
  • propionaldehyde