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Stereospecific Nucleophilic Substitution with Arylboronic Acids as Nucleophiles in the Presence of a CONH Group
Author(s) -
Tian Duanshuai,
Li Chengxi,
Gu Guoxian,
Peng Henian,
Zhang Xumu,
Tang Wenjun
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201712829
Subject(s) - chemistry , stereospecificity , nucleophile , nucleophilic substitution , substitution reaction , aryl , enantioselective synthesis , leaving group , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl
Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition‐metal‐free coupling between chiral α‐aryl‐α‐mesylated acetamides and arylboronic acids provided access to a series of chiral α,α‐diaryl acetamides with excellent enantioselectivity and moderate to good yields. The CONH functionality proved to be crucial for bridging the reactants and promoting the reaction. Efficient syntheses of a cannabinoid CB 1 receptor ligand, the antidepressant ( S )‐diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.