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Rhodium‐Catalyzed Enantioposition‐Selective Hydroarylation of Divinylphosphine Oxides with Aryl Boroxines
Author(s) -
Wang Zhe,
Hayashi Tamio
Publication year - 2018
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.201712572
Subject(s) - rhodium , chemistry , stereocenter , catalysis , aryl , moiety , char , selectivity , oxide , stereoselectivity , medicinal chemistry , organic chemistry , enantioselective synthesis , combustion , alkyl
Abstract The rhodium‐catalyzed hydroarylation of divinylphosphine oxides (RP(O)(CH=CH 2 ) 2 ) with aryl boroxines ((ArBO) 3 ) gives the corresponding monoarylation products (RP(O)(CH=CHAr)CH 2 CH 3 ) in high yields. One of the two vinyl groups in the phosphine oxide undergoes oxidative arylation while the other one is reduced to an ethyl moiety. These reactions proceed with high selectivity in terms of the enantiotopic vinyl groups in the presence of ( R )‐DTBM‐segphos/Rh to give the P‐stereogenic monoarylation products with high enantioselectivity.