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Diastereoselective C−H Bond Amination for Disubstituted Pyrrolidines
Author(s) -
Iovan Diana A.,
Wilding Matthew J. T.,
Baek Yunjung,
Hennessy Elisabeth T.,
Betley Theodore A.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201708519
Subject(s) - amination , chemistry , alkoxide , selectivity , catalysis , combinatorial chemistry , organic chemistry , medicinal chemistry
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(OEt 2 ) 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.