Diastereoselective C-H Bond Amination for Disubstituted Pyrrolidines.

Authors :: Iovan DA
Wilding MJT
Baek Y
Hennessy ET
Betley TA
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2017 Dec 04; Vol. 56 (49), pp. 15599-15602. Date of Electronic Publication: 2017 Nov 08.
Publication Year :: 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 ( <superscript>Ad</superscript> L)FeCl(OEt <subscript>2</subscript> ) 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.<br /> (© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)