Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines

Roohollah Kazem Shiroodi; Claudia I Rivera Vera; Alexander S Dudnik; Vladimir Gevorgyan

doi:10.1016/j.tetlet.2015.01.006

Synthesis of furans and pyrroles via migratory and double migratory cycloisomerization reactions of homopropargylic aldehydes and imines

Tetrahedron Lett. 2015 Jun 3;56(23):3251-3254. doi: 10.1016/j.tetlet.2015.01.006.

Authors

Roohollah Kazem Shiroodi¹, Claudia I Rivera Vera¹, Alexander S Dudnik¹, Vladimir Gevorgyan¹

Affiliation

¹ Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor Street, Chicago, IL 60607-7061, United States.

Abstract

A novel gold-catalyzed divergent sysnthesis of furans and pyrroles employing readily available homopropargylic aldehydes and imines have been developed. The regiochemical outcome of this reaction is dependent on the substituent on the terminal alkyne of substrate. Thus, substrates possessing alkyl and aryl substituent at the alkyne moiety produce 2,3,5-substituted furans and pyrroles via a migratory cycloisomerizaton reaction. Whereas, their silicon analogues are capable to undergo a double migratory process leading to 2,3,4-substituted heterocycles.

Keywords: Cycloisomerization; Double migration; Gold catalyst; Heterocycles; Silicon migration.

Grants and funding

R01 GM064444/GM/NIGMS NIH HHS/United States