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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.