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Diastereoselective C-H Bond Amination for Disubstituted Pyrrolidines.

ABSTRACT: We report herein the improved diastereoselective synthesis of 2,5-disubstituted pyrrolidines from aliphatic azides. Experimental and theoretical studies of the C-H amination reaction mediated by the iron dipyrrinato complex (Ad L)FeCl(OEt2 ) provided a model for diastereoinduction and allowed for systematic variation of the catalyst to enhance selectivity. Among the iron alkoxide and aryloxide catalysts evaluated, the iron phenoxide complex exhibited superior performance towards the generation of syn 2,5-disubstituted pyrrolidines with high diastereoselectivity.

SUBMITTER: Iovan DA

PROVIDER: S-EPMC5821116 | biostudies-literature | 2017 Dec

REPOSITORIES: biostudies-literature

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Diastereoselective C-H Bond Amination for Disubstituted Pyrrolidines.

Iovan Diana A DA Wilding Matthew J T MJT Baek Yunjung Y Hennessy Elisabeth T ET Betley Theodore A TA

Angewandte Chemie (International ed. in English) 20171108 49

We report herein the improved diastereoselective synthesis of 2,5-disubstituted pyrrolidines from aliphatic azides. Experimental and theoretical studies of the C-H amination reaction mediated by the iron dipyrrinato complex (Ad L)FeCl(OEt2 ) provided a model for diastereoinduction and allowed for systematic variation of the catalyst to enhance selectivity. Among the iron alkoxide and aryloxide catalysts evaluated, the iron phenoxide complex exhibited superior performance to ...[more]

PMID: 29024289

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