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Chain Walking of Allylrhodium Species Towards Esters During Rhodium-Catalyzed Nucleophilic Allylations of Imines.

ABSTRACT: Allylrhodium species derived from ?-trifluoroboryl ?,?-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.

SUBMITTER: Martinez JI

PROVIDER: S-EPMC4736453 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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Chain Walking of Allylrhodium Species Towards Esters During Rhodium-Catalyzed Nucleophilic Allylations of Imines.

Martínez Jose I JI Smith Joshua J JJ Hepburn Hamish B HB Lam Hon Wai HW

Angewandte Chemie (International ed. in English) 20151203 3

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. ...[more]

PMID: 26756445

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