Premium
Imidate–Phosphanes as Highly Versatile N,P Ligands and Their Application in Palladium‐Catalyzed Asymmetric Allylic Alkylation Reactions
Author(s) -
Noël Timothy,
Bert Katrien,
Van der Eycken Erik,
Van der Eycken Johan
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201000238
Subject(s) - tsuji–trost reaction , chemistry , catalysis , nucleophile , alkylation , allylic rearrangement , palladium , combinatorial chemistry , substrate (aquarium) , enantioselective synthesis , yield (engineering) , organic chemistry , medicinal chemistry , oceanography , materials science , metallurgy , geology
Chiral imidate–phosphanes were developed as a new type of N,P ligands. These ligands are easily accessible through a one‐step procedure starting from a commercially available chiral aminophosphane and an imidate precursor. Excellent performance of the catalyst system was observed with various carbon nucleophiles in the Pd 0 ‐catalyzed asymmetric allylic alkylation (up to 99 % yield and >99 % ee ). Moreover, good to excellent enantioselectivities could also be obtained in the allylic alkylation of more difficult linear unhindered substrates and cyclic substrates, demonstrating that this new catalyst system has a broad substrate scope.