Iridium‐Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides | Zendy

Hamilton James Y. | Zendy; Sarlah David | Zendy; Carreira Erick M. | Zendy

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Iridium‐Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides

Author(s) -

Hamilton James Y.,

Sarlah David,

Carreira Erick M.

Publication year - 2015

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.201501851

Subject(s) - enantioselective synthesis , iridium , tsuji–trost reaction , allylic rearrangement , alkylation , olefin fiber , nucleophile , chemistry , catalysis , bromide , combinatorial chemistry , reagent , substitution reaction , alkyl , organic chemistry

Iridium‐catalyzed enantioselective allylic alkylation of branched racemic carbonates with functionalized alkylzinc bromide reagents is described. Enabled by a chiral Ir/(P,olefin) complex, the method described allows allylic substitution with various primary and secondary alkyl nucleophiles with excellent regio‐ and enantioselectivities. The developed reaction was showcased in a concise, asymmetric synthesis of (−)‐preclamol.

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