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The isomerization of allylrhodium intermediates in the rhodium-catalyzed nucleophilic allylation of cyclic imines.

ABSTRACT: 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.

SUBMITTER: Hepburn HB

PROVIDER: S-EPMC4497600 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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The isomerization of allylrhodium intermediates in the rhodium-catalyzed nucleophilic allylation of cyclic imines.

Hepburn Hamish B HB Lam Hon Wai HW

Angewandte Chemie (International ed. in English) 20140909 43

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. ...[more]

PMID: 25205604

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