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Asymmetric Synthesis of Tertiary and Secondary Cyclopropyl Boronates via Cyclopropanation of Enantioenriched Alkenyl Boronic Esters. 2022

Álvaro Gutiérrez-Bonet, and Stasik Popov, and Marion H Emmert, and Jonathan M E Hughes, and Andrew F Nolting, and Serge Ruccolo, and Yunyi Wang
Process Research & Development, Merck Research Laboratories (MRL), Merck & Company, Incorporated, West Point, Pennsylvania 19486, United States.

The cyclopropanation of alkenyl boronates and subsequent derivatization of the boronate handle are a convenient strategy to quickly build molecular complexity and access diverse compounds with a high sp3 fraction. Herein, we describe the asymmetric cyclopropanation of enantioenriched hydrobenzoin-derived alkenyl boronic esters toward the synthesis of tertiary and secondary cyclopropyl boronates.

UI MeSH Term Description Entries
D001895 Boron A trace element with the atomic symbol B, atomic number 5, and atomic weight [10.806; 10.821]. Boron-10, an isotope of boron, is used as a neutron absorber in BORON NEUTRON CAPTURE THERAPY. Boron-11,Boron 11
D001897 Boronic Acids Inorganic or organic compounds that contain the basic structure RB(OH)2. Boronic Acid,Acid, Boronic,Acids, Boronic
D004952 Esters Compounds derived from organic or inorganic acids in which at least one hydroxyl group is replaced by an –O-alkyl or another organic group. They can be represented by the structure formula RCOOR’ and are usually formed by the reaction between an acid and an alcohol with elimination of water. Ester
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer

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