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Chain Walking of Allylrhodium Species Towards Esters During Rhodium‐Catalyzed Nucleophilic Allylations of Imines
Author(s) -
Martínez Jose I.,
Smith Joshua J.,
Hepburn Hamish B.,
Lam Hon Wai
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508964
Subject(s) - stereocenter , nucleophile , chemistry , alkene , diene , moiety , rhodium , chirality (physics) , catalysis , ligand (biochemistry) , stereochemistry , nucleophilic addition , enantioselective synthesis , combinatorial chemistry , organic chemistry , receptor , biochemistry , natural rubber , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
Allylrhodium species derived from δ‐trifluoroboryl β,γ‐unsaturated esters undergo chain walking towards the ester moiety. The resulting allylrhodium species react with imines to give products containing two new stereocenters and a Z ‐alkene. By using a chiral diene ligand, products can be obtained with high enantioselectivities, where a pronounced matched/mismatched effect with the chirality of the allyltrifluoroborate is evident.