Origin of enantioselection in Hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL

Org Lett. 2008 Jul 3;10(13):2749-52. doi: 10.1021/ol800875k. Epub 2008 May 29.

Abstract

The asymmetric hetero-Diels-Alder reaction of benzaldehyde with 1-dimethylamino-3- tert-butyldimethylsiloxy butadiene catalyzed by ( R, R)-1-Np-TADDOL was studied using computational methods. A theoretical rationale was developed through the combined use of molecular mechanics and ONIOM(B3LYP/6-31G(d):AM1) calculations. The origins of stereoselection in this process were identified, and excellent correlation between experiment and theory was found.

Publication types

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

MeSH terms

  • Aldehydes / chemistry
  • Catalysis
  • Dioxolanes / chemistry*
  • Methanol / analogs & derivatives*
  • Methanol / chemistry
  • Models, Molecular
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Stereoisomerism

Substances

  • Aldehydes
  • Dioxolanes
  • Naphthalenes
  • alpha,alpha,alpha',alpha'-tetraaryl-1,3-dioxolane-4,5-dimethanol
  • naphthyl-TADDOL
  • Methanol