Vinylogous aldol products from chiral crotylsilanes obtained by enantioselective Rh(II) and Cu(I) carbenoid Si-H insertion

Org Lett. 2010 May 7;12(9):2112-5. doi: 10.1021/ol100604m.

Abstract

Enantioenriched homoallylic ethers containing a alpha,beta-unsaturated ester (syn-vinylogous aldol products) were directly accessed by Lewis acid catalyzed crotylation utilizing chiral silane 2. The reagents were prepared by enantioselective Si-H insertion to an alpha-diazovinylacetates using Davies' Rh(2)(DOSP)(4) catalyst or chiral Cu(I) Schiff base complex.

Publication types

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

MeSH terms

  • Aldehydes / chemistry*
  • Copper / chemistry*
  • Hydrogen / chemistry*
  • Methane / analogs & derivatives*
  • Methane / chemistry
  • Rhenium / chemistry*
  • Silanes / chemistry*
  • Silicones / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Silanes
  • Silicones
  • crotylsilane
  • carbene
  • Rhenium
  • Copper
  • Hydrogen
  • 3-hydroxybutanal
  • Methane