Imidate–Phosphanes as Highly Versatile N,P Ligands and Their Application in Palladium‐Catalyzed Asymmetric Allylic Alkylation Reactions | Zendy

Noël Timothy | Zendy; Bert Katrien | Zendy; Van der Eycken Erik | Zendy; Van der Eycken Johan | Zendy

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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.

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