Work

Diastereoselective C−H Bond Amination for Disubstituted Pyrrolidines

Year: 2017

Type: article

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 (AdL)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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.201708519

Authors: Diana A. Iovan, Matthew J. T. Wilding, Yunjung Baek, Elisabeth T. Hennessy, Theodore A. Betley

Institution: Harvard University

Language: English

Topic: Synthesis and Catalytic Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Science Foundation, Foundation for the National Institutes of Health, National Institute of General Medical Sciences

Awards: Correlation of electronic structure to iron catalyzed C-H bond functionalization, G2798164012, CAREER: Iron mediated catalytic C-H bond functionalization