You are currently viewing the abstract.
View Full TextLog in to view the full text
AAAS login provides access to Science for AAAS members, and access to other journals in the Science family to users who have purchased individual subscriptions.
Register for free to read this article
As a service to the community, this article is available for free. Existing users log in.
More options
Download and print this article for your personal scholarly, research, and educational use.
Buy a single issue of Science for just $15 USD.
Independent Chiral Catalysts
Synthetic catalysts can be prepared in their mirror-image form and thereby furnish the mirror-image (enantiomer) of the reaction product. In practice, however, this versatility is largely limited to products featuring a single stereocenter that accounts for the dissymmetry. Krautwald et al. (p. 1065; see the Perspective by Schindler and Jacobsen) now report a pair of chiral catalysts—an iridium complex and an amine—that operate in concert to facilitate carbon-carbon bond formation, while retaining independent stereoselectivity toward their respective sides of the bond.
Abstract
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.