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J. Org. Chem. 2021, 86 (20), 14061–14068

DOI: 10.1021/acs.joc.1c00977

Ripenko V.; Vysochyn D.; Klymov I.; Zhersh S.; Mykhailiuk P.

In flow photochemical addition of propellane to diacetyl allowed construction of the bicyclo[1.1.1]pentane (BCP) core in a 1 kg scale within 1 day. Haloform reaction of the formed diketone in batch afforded bicyclo[1.1.1]pentane-1,3-dicarboxylic acid in a multigram amount. Representative gram scale transformations of the diacid were also performed to obtain various BCP-containing building blocks—alcohols, acids, amines, trifluoroborates, amino acids, etc.—for medicinal chemistry.

 

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