B(C6F5)3‑Catalyzed Formal (n + 3) (n = 5 and 6) Cycloaddition of Bicyclo[1.1.0]butanes to Medium Bicyclo[n.1.1]alkanes

Herein, a B­(C6F5)3-catalyzed formal (n + 3) (n = 5 and 6) cycloaddition of bicyclo[1.1.0]­butanes (BCBs) with imidazolidines/hexahydropyrimidines is described. The reaction provides a modular, atom-economical, and efficient strategy to two libraries of synthetically challenging medium-bridged rings...

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Bibliographic Details
Published in:Organic letters 2024-05, Vol.26 (19), p.4104-4110
Main Authors: Yang, Liangliang, Wang, Haiyang, Lang, Ming, Wang, Jian, Peng, Shiyong
Format: Article
Language:English
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Summary:Herein, a B­(C6F5)3-catalyzed formal (n + 3) (n = 5 and 6) cycloaddition of bicyclo[1.1.0]­butanes (BCBs) with imidazolidines/hexahydropyrimidines is described. The reaction provides a modular, atom-economical, and efficient strategy to two libraries of synthetically challenging medium-bridged rings, 2,5-diazabicyclo[5.1.1]­nonanes and 2,6-diazabicyclo[6.1.1]­decanes, in moderate to excellent yields. This reaction also features simple operation, mild reaction conditions, and broad substrate scope. A scale-up experiment and various synthetic transformations of products further highlight the synthetic utility.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.4c01219