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Enantioselective Copper‐Catalyzed Carboetherification of Unactivated Alkenes
Author(s) -
Bovino Michael T.,
Liwosz Timothy W.,
Kendel Nicole E.,
Miller Yan,
Tyminska Nina,
Zurek Eva,
Chemler Sherry R.
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201402462
Subject(s) - enantioselective synthesis , alkene , catalysis , chemistry , ring (chemistry) , intermolecular force , copper , combinatorial chemistry , stereochemistry , organic chemistry , molecule
Chiral 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.