Iridium-catalyzed enantioselective allylic alkylation with functionalized organozinc bromides

James Y. Hamilton, David Sarlah, Erick M. Carreira

Research output: Contribution to journalArticlepeer-review

Abstract

Iridium-catalyzed enantioselective allylic alkylation of branched racemic carbonates with functionalized alkylzinc bromide reagents is described. Enabled by a chiral Ir/(P,olefin) complex, the method described allows allylic substitution with various primary and secondary alkyl nucleophiles with excellent regio- and enantioselectivities. The developed reaction was showcased in a concise, asymmetric synthesis of (-)-preclamol. An Ir/(P,olefin) complex catalyzes the title reaction and the method provides a variety of allylated products with excellent regio- and stereoselectivities. The utility of the coupling is demonstrated in a catalytic enantioselective synthesis of a preclinical drug (-)-preclamol. Boc=tert-butyloxycarbonyl, cod=1,5-cyclooctadiene.

Original languageEnglish (US)
Pages (from-to)7644-7647
Number of pages4
JournalAngewandte Chemie - International Edition
Volume54
Issue number26
DOIs
StatePublished - Jun 1 2015
Externally publishedYes

Keywords

  • alkylation
  • allylic compounds
  • enantioselectivity
  • iridium
  • zinc

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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