Enantio- and diastereodivergent dual catalysis: α-Allylation of branched aldehydes

Simon Krautwald, David Sarlah, Michael A. Schafroth, Erick M. Carreira

Research output: Contribution to journalArticlepeer-review


An important challenge in asymmetric synthesis is the development of fully stereodivergent strategies to access the full complement of stereoisomers of products bearing multiple stereocenters. In the ideal case, where four products are possible, applying distinct catalysts to the same set of starting materials under identical conditions would in a single step afford any given stereoisomer. Herein, we describe the realization of this concept in a fully stereodivergent dual-catalytic synthesis of γ,δ-unsaturated aldehydes bearing vicinal quaternary/tertiary stereogenic centers. The reaction is enabled by chiral iridium and amine catalysts, which activate the allylic alcohol and aldehyde substrates, respectively. Each catalyst exerts high local stereocontrol irrespective of the other's inherent preference.

Original languageEnglish (US)
Pages (from-to)1065-1068
Number of pages4
Issue number6136
StatePublished - May 31 2013
Externally publishedYes

ASJC Scopus subject areas

  • General


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