Catalyst-directed diastereo- and site-selectivity in successive nucleophilic and electrophilic allylations of chiral 1,3-diols: protecting-group-free synthesis of substituted pyrans

Chemistry. 2014 Oct 6;20(41):13382-9. doi: 10.1002/chem.201404065. Epub 2014 Aug 28.

Abstract

The iridium-catalyzed, protecting group-free synthesis of 4-hydroxy-2,6-cis- or trans-pyrans through successive nucleophilic and electrophilic allylations of chiral 1,3-diols occurs with complete levels of catalyst-directed diastereoselectivity in the absence of protecting groups, premetallated reagents, or discrete alcohol-to-aldehyde redox reactions.

Keywords: catalyst-directed diastereoselectivity; polyketides; protecting group-free reactions; pyran; transfer hydrogenation.

Publication types

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

MeSH terms

  • Alcohols / chemistry
  • Aldehydes / chemistry
  • Catalysis
  • Iridium / chemistry
  • Oxidation-Reduction
  • Pyrans / chemical synthesis
  • Pyrans / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Pyrans
  • Iridium