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

Christopher D. Anderson, Travis Dudding, Ruth Gordillo, K. N. Houk

Research output: Contribution to journalArticle

68 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original languageEnglish (US)
Pages (from-to)2749-2752
Number of pages4
JournalOrganic Letters
Volume10
Issue number13
DOIs
StatePublished - 2008

Fingerprint

Diels-Alder reactions
Molecular mechanics
Cycloaddition Reaction
butadiene
Computational methods
Mechanics
Experiments
benzaldehyde
1,3-butadiene
naphthyl-TADDOL

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Biochemistry
  • Molecular Medicine

Cite this

Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL. / Anderson, Christopher D.; Dudding, Travis; Gordillo, Ruth; Houk, K. N.

In: Organic Letters, Vol. 10, No. 13, 2008, p. 2749-2752.

Research output: Contribution to journalArticle

Anderson, Christopher D. ; Dudding, Travis ; Gordillo, Ruth ; Houk, K. N. / Origin of enantioselection in hetero-Diels-Alder reactions catalyzed by naphthyl-TADDOL. In: Organic Letters. 2008 ; Vol. 10, No. 13. pp. 2749-2752.
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