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Chiral Sulfoxide‐Olefin Ligands: Completely Switchable Stereoselectivity in Rhodium‐Catalyzed Asymmetric Conjugate Additions
Author(s) -
Chen Guihua,
Gui Jiangyang,
Li Liangchun,
Liao Jian
Publication year - 2011
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.201102586
Subject(s) - olefin fiber , stereoselectivity , rhodium , chemistry , catalysis , sulfoxide , ligand (biochemistry) , combinatorial chemistry , stereochemistry , organic chemistry , biochemistry , receptor
Have it both ways : A novel class of chiral sulfoxide‐olefin ligands was synthesized from a single chiral source. These ligands were evaluated in rhodium‐catalyzed 1,4‐additions of arylboronic acids to electron‐deficient olefins, and remarkable olefin‐directed reversal of stereoselectivity (up to >99 % ee, R isomer; 98 % ee, S isomer) was observed when the reversal ligand pair L1 (branched olefin) and L2 (linear olefin) were utilized (see scheme).