Schwegman Lundberg & Woessner, P.A.
Cu- and Ni-catalyzed decarboxylative borylation reactions
The invention is directed to methods of converting a carboxylic acid group in a compound, via a redox active ester, to a corresponding boronic ester by treatment with bis(pinacolato)diboron-alkyllithium complex in the presence of a ligand, a Ni(ll) salt or a copper salt, and an Mg(ll) salt, in the presence of an alkyllithium or a lithium hydroxide or alkoxide salt. The product pinacolato boronate ester can be cleaved to provide a boronic acid. The invention is also directed to methods of preparing various compounds of medical value comprising boronic acid groups, and to novel boronic-acid containing compounds of medicinal value, including an atorvastatin boronic acid analog, a vancomycin aglycone boronic acid analog, and boronic acid containing elastase inhibitors mCBK319, mCBK320, mCBK323, and RPX-7009.
THE SCRIPPS RESEARCH INSTITUTE
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C07B A61K C07F C07K B01J B01J A61K A61K B01J C07F
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Jie Tian Kristen Ann Manoj Arnab Kumar Chao Ming Phil Shan
Wang Qin Johnson Kumar Chatterjee Li Shang Baran Yu