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Synthesis of Chiral β‐Lactams by Pd‐Catalyzed Enantioselective Amidation of Methylene C(sp 3 )–H Bonds
Author(s) -
Zhou Tao,
Jiang MengXue,
Yang Xu,
Yue Qiang,
Han YeQiang,
Ding Yi,
Shi BingFeng
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201900533
Subject(s) - chemistry , enantioselective synthesis , methylene , intramolecular force , catalysis , nitrobenzene , reactivity (psychology) , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , medicine , alternative medicine , pathology
Summary of main observation and conclusion A Pd(II)‐catalyzed enantioselective intramolecular amidation of both benzylic and unbiased methylene C(sp 3 )−H bonds for the straightforward synthesis of chiral β‐lactams from aliphatic carboxamides is reported. The combination of 2‐pyridinylisopropyl (PIP) auxiliary with 3,3’‐substituted BINOL ligands is crucial for the enhancement of both reactivity and enantiocontrol of differentiating unbiased methylene C(sp 3 )−H bonds. The desired chemoselective C—N reductive elimination was achieved by employing 2‐fluoro‐1‐iodo‐4‐nitrobenzene as oxidant.