Catalytic, asymmetric hypervinylogous Mukaiyama aldol reactions of extended furan-based silyl enolates

Org Lett. 2011 Sep 2;13(17):4738-41. doi: 10.1021/ol2020626. Epub 2011 Aug 11.

Abstract

Virtually perfect transmittal of the enolate reactivity up to five conjugated double bonds from the origin allows a series of furan-based silyloxypolyenes to add to aldehyde carbonyls at the most distant point of the molecule. Denmark's axially chiral bisphosphoramide/SiCl(4) combination catalyzes these scantly precedented, long-range Mukaiyama-type vinylogous aldol reactions efficiently, providing a palette of extended γ-alkylidene butenolide carbinols with complete ω-site selectivity and good to excellent levels of enantioselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemical synthesis*
  • Alcohols / chemistry
  • Aldehydes / chemistry*
  • Amides / chemistry*
  • Catalysis
  • Chlorides / chemistry*
  • Furans / chemistry*
  • Molecular Structure
  • Phosphoramides
  • Phosphoric Acids / chemistry*
  • Silicon Compounds / chemistry*
  • Stereoisomerism

Substances

  • Alcohols
  • Aldehydes
  • Amides
  • Chlorides
  • Furans
  • Phosphoramides
  • Phosphoric Acids
  • Silicon Compounds
  • phosphoramide
  • silicon tetrachloride
  • furan