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Copper‐Catalyzed Enantioselective Allyl–Allyl Coupling between Allylic Boronates and Phosphates with a Phenol/N‐Heterocyclic Carbene Chiral Ligand
Author(s) -
Yasuda Yuto,
Ohmiya Hirohisa,
Sawamura Masaya
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201605125
Subject(s) - allylic rearrangement , stereocenter , enantioselective synthesis , carbene , chemistry , ligand (biochemistry) , catalysis , diene , medicinal chemistry , stereochemistry , organic chemistry , biochemistry , natural rubber , receptor
Copper‐catalyzed enantioselective allyl–allyl coupling between allylboronates and either Z ‐acyclic or cyclic allylic phosphates using a new chiral N‐heterocyclic carbene ligand, bearing a phenolic hydroxy, is reported. This reaction occurs with exceptional S N 2′‐type regioselectivities and high enantioselectivities to deliver chiral 1,5‐diene derivatives with a tertiary stereogenic center at the allylic/homoallylic position.