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A Stereospecific Ruthenium‐Catalyzed Allylic Alkylation
Author(s) -
Trost Barry M.,
Fraisse Pierre L.,
Ball Zachary T.
Publication year - 2002
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 - 10.1002/1521-3773(20020315)41:6<1059::aid-anie1059>3.0.co;2-5
Subject(s) - allylic rearrangement , ruthenium , regioselectivity , stereospecificity , nucleophile , chemistry , aryl , chirality (physics) , catalysis , tsuji–trost reaction , organic chemistry , combinatorial chemistry , physics , particle physics , alkyl , chiral symmetry breaking , nambu–jona lasinio model , quark
Good regioselectivity and chirality transfer for aryl‐substituted allyl units is achieved in allylic alkylations with a wide range of nucleophiles by using the highly active ruthenium catalyst 1 . This method provides a route to antidepressants such as (−)‐fluoxetine from ( S )‐ephedrine (see scheme; Cp*= η 5 ‐C 5 Me 5 , TBAT=tetrabutylammonium triphenyldifluorosilicate).