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Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.

ABSTRACT: Umpolung Amide Synthesis (UmAS) provides direct access to amides from an ?-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 ?-bromo nitroalkane donors, this protocol realizes the goal of enantioselective ?-amino amide and peptide synthesis based solely on catalytic methods.

SUBMITTER: Schwieter KE

PROVIDER: S-EPMC4168777 | biostudies-literature | 2014 Sep

REPOSITORIES: biostudies-literature

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Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.

Schwieter Kenneth E KE Shen Bo B Shackleford Jessica P JP Leighty Matthew W MW Johnston Jeffrey N JN

Organic letters 20140908 18

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 b ...[more]

PMID: 25198239

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