Theoretical explorations of enantioselective alkylation reactions of pyrroles and indoles organocatalyzed by chiral imidazolidinones

Ruth Gordillo, Jennifer Carter, K. N. Houk

Research output: Contribution to journalArticle

76 Citations (Scopus)

Abstract

The transition structures for MacMillan's alkylations of N-methylpyrrole by aldehydes catalyzed by chiral amine salts were explored with B3LYP/6-31G(d) density functional theory. These results provide an explanation of the enantioselectivities observed with these two catalysts.

Original languageEnglish (US)
Pages (from-to)1175-1185
Number of pages11
JournalAdvanced Synthesis and Catalysis
Volume346
Issue number9-10
DOIs
StatePublished - Aug 2004

Fingerprint

Indoles
Pyrroles
Enantioselectivity
Alkylation
Aldehydes
Amines
Density functional theory
Salts
Catalysts
N-methylpyrrole

Keywords

  • Alkylation reactions
  • Chiral imidazolidinones
  • Enantioselection
  • Hybrid density functional theory
  • Organic catalysis

ASJC Scopus subject areas

  • Chemistry (miscellaneous)
  • Organic Chemistry
  • Catalysis

Cite this

Theoretical explorations of enantioselective alkylation reactions of pyrroles and indoles organocatalyzed by chiral imidazolidinones. / Gordillo, Ruth; Carter, Jennifer; Houk, K. N.

In: Advanced Synthesis and Catalysis, Vol. 346, No. 9-10, 08.2004, p. 1175-1185.

Research output: Contribution to journalArticle

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