Publisher： John Wiley & Sons Inc
E-ISSN： 1521-3773|53|25|6383-6387
ISSN： 1433-7851
Source： ANGEWANDTE CHEMIE INTERNATIONAL EDITION, Vol.53, Iss.25, 2014-06, pp. : 6383-6387
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Abstract
AbstractChiral saturated oxygen heterocycles are important components of bioactive compounds. Cyclization of alcohols onto pendant alkenes is a direct route to their synthesis, but few catalytic enantioselective methods enabling cyclization onto unactivated alkenes exist. Herein reported is a highly efficient copper‐catalyzed cyclization of γ‐unsaturated pentenols which terminates in CC bond formation, a net alkene carboetherification. Both intra‐ and intermolecular CC bond formations are demonstrated, thus yielding functionalized chiral tetrahydrofurans as well as fused‐ring and bridged‐ring oxabicyclic products. Transition‐state calculations support a cis‐oxycupration stereochemistry‐determining step.
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