Enantioselective formal (3 + 3) cycloaddition of bicyclobutanes with nitrones enabled by asymmetric Lewis acid catalysis

Wen-Biao Wu, Bing Xu, Xue-Chun Yang, Feng Wu, Heng-Xian He, Xu Zhang and Jian-Jun Feng ()
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Wen-Biao Wu: Hunan University
Bing Xu: Fudan University
Xue-Chun Yang: Hunan University
Feng Wu: Hunan University
Heng-Xian He: Hunan University
Xu Zhang: Yangzhou University
Jian-Jun Feng: Hunan University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract The absence of catalytic asymmetric methods for synthesizing chiral (hetero)bicyclo[n.1.1]alkanes has hindered their application in new drug discovery. Here we demonstrate the achievability of an asymmetric polar cycloaddition of bicyclo[1.1.0]butane using a chiral Lewis acid catalyst and a bidentate chelating bicyclo[1.1.0]butane substrate, as exemplified by the current enantioselective formal (3 + 3) cycloaddition of bicyclo[1.1.0]butanes with nitrones. In addition to the diverse bicyclo[1.1.0]butanes incorporating an acyl imidazole group or an acyl pyrazole moiety, a wide array of nitrones are compatible with this Lewis acid catalysis, successfully assembling two congested quaternary carbon centers and a chiral aza-trisubstituted carbon center in the pharmaceutically important hetero-bicyclo[3.1.1]heptane product with up to 99% yield and >99% ee.

Date: 2024
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DOI: 10.1038/s41467-024-52419-x

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