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. 2020 Feb 26;142(8):3680-3685.
doi: 10.1021/jacs.9b12930. Epub 2020 Feb 12.

Boronate Ester Bullvalenes

Harshal D Patel  1 , Thanh-Huyen Tran  1 , Christopher J Sumby  1 , Lukáš F Pašteka  2 , Thomas Fallon  1
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Boronate Ester Bullvalenes

Harshal D Patel et al. J Am Chem Soc. .

Abstract

Boronate ester bullvalenes are now accessible in two to four operationally simple steps. This unlocks late-stage diversification through Suzuki cross-coupling reactions to give mono-, di-, and trisubstituted bullvalenes. Moreover, a linchpin strategy enables preprogrammed installation of two different substituents. Analysis of solution phase isomer distributions and single-crystal X-ray structures reveals that isomer preference in the crystal lattice is due to general shape selectivity.

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