Journal
SCIENCE
Volume 340, Issue 6136, Pages 1065-1068Publisher
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1237068
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Funding
- Swiss National Science Foundation [200020_135224]
- Fonds der Chemischen Industrie
- Cambridge Crystallographic Data Centre [CCDC 933469]
- Swiss National Science Foundation (SNF) [200020_135224] Funding Source: Swiss National Science Foundation (SNF)
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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 gamma,delta-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.
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