Enantioselective alkylation of acyclic α,α-disubstituted tributyltin enolates catalyzed by a {Cr(salen)} complex

Abigail G. Doyle, Eric N. Jacobsen

Research output: Contribution to journalArticle

68 Scopus citations

Abstract

Straighten out the mixture: A dynamic mixture of acyclic isomers of tributyltin enolates undergoes a {Cr(salen)}-catalyzed alkylation reaction to generate methyl ketones that contain α-carbonyl quaternary stereocenters in high yield and enantioselectivity (salen = N,N′-bis(salicylidene) ethylenediamine dianion). A mechanism is proposed which involves halide activation by a cationic metal complex. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)3701-3705
Number of pages5
JournalAngewandte Chemie - International Edition
Volume46
Issue number20
DOIs
StatePublished - 2007
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Alkylation
  • Asymmetric catalysis
  • Chromium
  • Enolates
  • N,O ligands

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