Work

Umpolung Amide Synthesis Using Substoichiometric N -Iodosuccinimide (NIS) and Oxygen as a Terminal Oxidant

Year: 2014

Type: article

Abstract: Umpolung Amide Synthesis (UmAS) provides direct access to amides from an α-bromo nitroalkane and an amine. Based on its mechanistic bifurcation after convergent C-N bond formation, depending on the absence or presence of oxygen, UmAS using substoichiometric N-iodosuccinimide (NIS) under aerobic conditions has been developed. In combination with the enantioselective preparation of α-bromo nitroalkane donors, this protocol realizes the goal of enantioselective α-amino amide and peptide synthesis based solely on catalytic methods.

Source: Organic Letters

DOI: 10.1021/ol502089v

Authors: Kenneth E. Schwieter, Bo Shen, Jessica P. Shackleford, Matthew W. Leighty, Jeffrey N. Johnston

Institution: Vanderbilt University

Language: English

Topic: Oxidative Organic Chemistry Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

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