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

Autor: Wu WB; State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, P. R. China.; School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, P. R. China.; School of Physics and Chemistry, Hunan First Normal University, Changsha, P. R. China., Xu B; Department of Chemistry, Fudan University, Shanghai, P.R. China., Yang XC; State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, P. R. China., Wu F; State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, P. R. China., He HX; State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, P. R. China., Zhang X; School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, P. R. China., Feng JJ; State Key Laboratory of Chemo/Biosensing and Chemometrics, Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha, P. R. China. jianjunfeng@hnu.edu.cn.
Jazyk: angličtina
Zdroj: Nature communications [Nat Commun] 2024 Sep 13; Vol. 15 (1), pp. 8005. Date of Electronic Publication: 2024 Sep 13.
DOI: 10.1038/s41467-024-52419-x
Abstrakt: 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.
(© 2024. The Author(s).)
Databáze: MEDLINE
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