Rhodium‐Catalyzed Enantioselective 1,2‐Addition of Aluminum Organyl Compounds to Cyclic Enones | Zendy

Siewert Jürgen | Zendy; Sandmann René | Zendy; von Zezschwitz Paultheo | Zendy

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Rhodium‐Catalyzed Enantioselective 1,2‐Addition of Aluminum Organyl Compounds to Cyclic Enones

Author(s) -

Siewert Jürgen,

Sandmann René,

von Zezschwitz Paultheo

Publication year - 2007

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.200701087

Subject(s) - enantioselective synthesis , chemoselectivity , rhodium , ligand (biochemistry) , chemistry , catalysis , stereoselectivity , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , biochemistry , receptor

A question of the ligand : The chemoselectivity of the rhodium‐catalyzed addition of AlMe 3 to cyclohex‐2‐enone is guided by the type of ligand used. Whereas use of an achiral {Rh(cyclooctadiene)} complex leads to a 1,4‐addition, use of a {Rh(binap)} species gives highly enantioselective 1,2‐additions. This unprecedented reaction can be used for stereoselective 1,2‐methylations and arylations of cyclic enones (see scheme).

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