Photochemically Driven Tandem Process in the Construction of a Biscyclopropylcage from 2,5-Dimethoxy- p -benzoquinone and Terminal Acetylenes

A photochemical two-step one-pot synthesis of novel biscyclopropyl-box-shaped compounds via the reaction of 2,5-dimethoxy- -benzoquinone and monosubstituted alkynes is reported. The reaction mechanism for a process in which six new C-C bonds are formed is explored by means of experimental and comput...

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Bibliographic Details
Published in:Organic letters 2020-06, Vol.22 (11), p.4527-4531
Main Authors: Álvarez-García, Jonathan, Rubio-Pisabarro, Víctor, Silva-López, Carlos, Cid, María Magdalena
Format: Article
Language:English
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Summary:A photochemical two-step one-pot synthesis of novel biscyclopropyl-box-shaped compounds via the reaction of 2,5-dimethoxy- -benzoquinone and monosubstituted alkynes is reported. The reaction mechanism for a process in which six new C-C bonds are formed is explored by means of experimental and computational techniques. The whole process occurs with complete selectivity, and only one densely decorated diastereomer is obtained; such a degree of control and substitution makes for a rather powerful and complexity-building process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c01554