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Gold-Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters.

ABSTRACT: Homogeneous gold catalysts are interesting as they can act as potent carbophilic Lewis acids to activate the ? bonds of alkynes, allenes, and alkenes. Many impressive applications for the formation of C-C or C-heteroatom bonds have been found due to the excellent functional group compatibility of these catalysts and the air and moisture tolerance of their reactions. Here, we have developed gold-catalyzed novel intramolecular cycloisomerizations of nitrogen or oxygen-tethered cyclopropenes with propargylic esters. The reaction proceeded through different pathways according to different substituent styles, affording 5-azaspiro[2.5]oct-7-enes and bicyclo[4.1.0]heptanes.

SUBMITTER: Zhu PL 

PROVIDER: S-EPMC4906491 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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Gold-Catalyzed Intramolecular Cyclizations of Cyclopropenes with Propargylic Esters.

Zhu Peng-Long PL   Tang Xiang-Ying XY   Shi Min M  

ChemistryOpen 20151012 1

Homogeneous gold catalysts are interesting as they can act as potent carbophilic Lewis acids to activate the π bonds of alkynes, allenes, and alkenes. Many impressive applications for the formation of C-C or C-heteroatom bonds have been found due to the excellent functional group compatibility of these catalysts and the air and moisture tolerance of their reactions. Here, we have developed gold-catalyzed novel intramolecular cycloisomerizations of nitrogen or oxygen-tethered cyclopropenes with p  ...[more]

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