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

Kenneth E. Schwieter | Zendy; Bo Shen | Zendy; Jessica P. Shackleford | Zendy; Matthew W. Leighty | Zendy; Jeffrey N. Johnston | Zendy

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

Author(s) -

Kenneth E. Schwieter,

Bo Shen,

Jessica P. Shackleford,

Matthew W. Leighty,

Jeffrey N. Johnston

Publication year - 2014

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/ol502089v

Subject(s) - umpolung , chemistry , amide , enantioselective synthesis , amine gas treating , catalysis , combinatorial chemistry , peptide bond , convergent synthesis , stereochemistry , peptide , organic chemistry , nucleophile , biochemistry

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.

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