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The Isomerization of Allylrhodium Intermediates in the Rhodium‐Catalyzed Nucleophilic Allylation of Cyclic Imines
Author(s) -
Hepburn Hamish B.,
Lam Hon Wai
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201407233
Subject(s) - rhodium , isomerization , chemistry , diene , nucleophilic addition , nucleophile , catalysis , organic chemistry , natural rubber
Allylrhodium species generated from potassium allyltrifluoroborates can undergo isomerization by 1,4‐rhodium(I) migration to give more complex isomers, which then react with cyclic imines to provide products with up to three new stereochemical elements. High enantioselectivities are obtained using chiral diene–rhodium complexes.