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

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 cond...

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Bibliographic Details
Published in:Organic letters 2014-09, Vol.16 (18), p.4714-4717
Main Authors: Schwieter, Kenneth E, Shen, Bo, Shackleford, Jessica P, Leighty, Matthew W, Johnston, Jeffrey N
Format: Article
Language:English
Subjects:
Alkanes - chemistry
Amides - chemical synthesis
Amides - chemistry
Amines - chemistry
Catalysis
Combinatorial Chemistry Techniques
Hydrocarbons, Brominated - chemistry
Letter
Molecular Structure
Nitro Compounds - chemistry
Oxygen - chemistry
Succinimides - chemistry
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502089v