Pyran annulation: asymmetric synthesis of 2,6-disubstituted-4-methylene tetrahydropyrans

Org Lett. 2002 Apr 4;4(7):1189-92. doi: 10.1021/ol025645d.

Abstract

[reaction: see text] A reaction process for the asymmetric construction of a variety of cis or trans disubstituted pyrans is described. This sequences allows for the asymmetric convergent union of two aldehydes with silyl-stannane reagent 1 in a two-step process: catalytic asymmetric allylation of the first aldehyde using 1 with a BITIP catalyst, followed by reaction of the alcohol so obtained with a second aldehyde and TMSOTf.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Indicators and Reagents
  • Pyrans / chemistry*
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Pyrans