Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.
Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.
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DOI：
10.1021/ol502089v
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发表时间：
2014-09-19
期刊：
影响因子：
5.2
通讯作者：
Johnston, Jeffrey N.
中科院分区：
文献类型：
--
作者：
Schwieter, Kenneth E.;Shen, Bo;Shackleford, Jessica P.;Leighty, Matthew W.;Johnston, Jeffrey N.
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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