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Diastereoselective C-H Bond Amination for Disubstituted Pyrrolidines
Diana A Iovan1, Matthew J T Wilding1, Yunjung Baek1
1Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA, 02138, USA.
Angewandte Chemie (International Ed. in English)
|October 13, 2017
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.