Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 24, Pages 7176-7180Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201712829
Keywords
arylboronic acids; enantioselectivity; nucleophilic substitution; stereospecificity; alpha,alpha,-diaryl acetamides
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Funding
- Strategic Priority Research Program of the Chinese Academy of Sciences [XDB20000000]
- CAS [QYZDY-SSW-SLH029]
- K.C. Wong Education Foundation
- NSFC [21572246, 21725205, 21432007]
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Stereospecific nucleophilic substitution was achieved for the first time with arylboronic acids as nucleophiles. This transition-metal-free coupling between chiral -aryl--mesylated acetamides and arylboronic acids provided access to a series of chiral ,-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 CB1 receptor ligand, the antidepressant (S)-diclofensine, and a key chiral building block of the inhibitor implitapide were successfully accomplished by using this method.
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