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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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201712829
Subject(s) - stereospecificity , nucleophile , group (periodic table) , substitution (logic) , nucleophilic substitution , chemistry , substitution reaction , medicinal chemistry , stereochemistry , organic chemistry , philosophy , catalysis , linguistics
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.