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Palladium‐Catalyzed Asymmetric Quaternary Stereocenter Formation
Author(s) -
Gottumukkala Aditya L.,
Matcha Kiran,
Lutz Martin,
de Vries Johannes G.,
Minnaard Adriaan J.
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201200694
Subject(s) - stereocenter , palladium , catalysis , conjugate , chemistry , enantiomer , palladium catalyst , combinatorial chemistry , organic chemistry , enantioselective synthesis , mathematics , mathematical analysis
Abstract An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β‐disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl 2 , PhBOX, and AgSbF 6 , and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (−)‐α‐cuparenone has been prepared in only two steps.