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Efficient Suzuki‐Type Cross‐Coupling of Enantiomerically Pure Cyclopropylboronic Acids
Author(s) -
Zhou ShaoMan,
Deng MinZhi,
Xia LiJun,
Tang MingHua
Publication year - 1998
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/(sici)1521-3773(19981102)37:20<2845::aid-anie2845>3.0.co;2-u
Subject(s) - electrophile , enantiomer , absolute configuration , optically active , asymmetric carbon , tartaric acid , chemistry , carbon atom , enantiomeric excess , coupling (piping) , palladium , coupling reaction , atom (system on chip) , catalysis , medicinal chemistry , enantioselective synthesis , stereochemistry , organic chemistry , materials science , ring (chemistry) , computer science , metallurgy , citric acid , embedded system
Optically active cyclopropanes (e.g. 1 ) can be prepared by the use of tartaric acid derivatives as chiral auxiliaries in the palladium‐catalyzed cross‐coupling of optically active cyclopropylboronic acids with electrophiles. The absolute configuration of the chiral carbon atom is retained, and the reaction proceeds with good yields and enantiomeric excesses. R=H, p ‐Ph, o ‐CO 2 CH 3 , p ‐CO 2 CH 3 , p ‐NO 2 , o ‐OCH 3 , m ‐OCH 3 .