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(Reference retrieved automatically from Web of Science through information on FAPESP grant and its corresponding number as mentioned in the publication by the authors.)

Hydroamination versus Allylic Amination in Iridium-Catalyzed Reactions of Allylic Acetates with Amines: 1,3-Aminoalcohols via Ester-Directed Regioselectivity

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Author(s):
Kim, Seung Wook [1] ; Wurm, Thomas [1] ; Brito, Gilmar A. [1] ; Jung, Woo-Ok [1] ; Zbieg, Jason R. [2] ; Stivala, Craig E. [2] ; Krische, Michael J. [1]
Total Authors: 7
Affiliation:
[1] Univ Texas Austin, Dept Chem, Austin, TX 78712 - USA
[2] Genentech Inc, Discovery Chem, 1 DNA Way, San Francisco, CA 94080 - USA
Total Affiliations: 2
Document type: Journal article
Source: Journal of the American Chemical Society; v. 140, n. 29, p. 9087-9090, JUL 25 2018.
Web of Science Citations: 9
Abstract

In the presence of a neutral dppf-modified iridium catalyst and Cs2CO3, linear allylic acetates react with primary amines to form products of hydroamination with complete 1,3-regioselectivity. The collective data, including deuterium labeling studies, corroborate a catalytic mechanism involving rapid, reversible acetate directed aminoiridation with inner-sphere/outer-sphere crossover followed by turnover-limiting proto-demetalation mediated by amine. (AU)

FAPESP's process: 17/00734-5 - Catalytic synthesis of Type II polyketides via Hydrogen-Mediated C-C bond formation
Grantee:Gilmar Araujo Brito Junior
Support type: Scholarships abroad - Research Internship - Post-doctor