A unique approach to aldol products for the creation of all-carbon quaternary stereocentres

Nat Chem. 2009 May;1(2):128-32. doi: 10.1038/nchem.131. Epub 2009 Mar 29.

Abstract

Among the challenges facing asymmetric synthesis the selective construction of quaternary stereogenic centres, particularly those bearing all-carbon substituents, stands out. The aldol reaction has the potential to create such stereocentres, but, despite the many advances in this field, a highly selective and efficient procedure has remained elusive. Here we show that, by choosing an alternative retrosynthetic approach, such products can be prepared in a highly selective fashion. Through the consecutive addition of several organometallic derivatives, an allylzinc reagent is prepared and, on addition to an aldehyde, an aldol-type product is created. The one-pot operation involves the construction of three new carbon-carbon bonds and the formation of an all-carbon quaternary stereocentre. The products of the reaction are amenable to downstream modification, and the procedure should find applications in the fields of natural product synthesis and drug discovery.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldehydes / chemistry*
  • Biological Products / chemical synthesis
  • Biological Products / chemistry
  • Carbon / chemistry*
  • Crystallography, X-Ray
  • Hydrolysis
  • Molecular Conformation
  • Stereoisomerism

Substances

  • Aldehydes
  • Biological Products
  • Carbon
  • 3-hydroxybutanal

Associated data

  • PubChem-Substance/57280285
  • PubChem-Substance/57280286
  • PubChem-Substance/57280287
  • PubChem-Substance/57280288
  • PubChem-Substance/57280289
  • PubChem-Substance/57280290
  • PubChem-Substance/57280291
  • PubChem-Substance/57280292
  • PubChem-Substance/57280293
  • PubChem-Substance/57280294
  • PubChem-Substance/57280295
  • PubChem-Substance/57280296
  • PubChem-Substance/57280297
  • PubChem-Substance/57280298
  • PubChem-Substance/57280299
  • PubChem-Substance/57280300
  • PubChem-Substance/57280301
  • PubChem-Substance/57280302
  • PubChem-Substance/57280303
  • PubChem-Substance/57280304
  • PubChem-Substance/57280305
  • PubChem-Substance/57280306