Jump to main content
Jump to site search


Thiourea participation in [3+2] cycloaddition with donor–acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes

Author affiliations

Abstract

The Yb(OTf)3-catalyzed [3+2] cycloaddition of donor–acceptor cyclopropanes with thiourea offers an efficient route to diverse 2-amino-4,5-dihydrothiophenes (up to 92% yield), in which optically active 2-amino-dihydrothiophenes can be produced from enantiomerically pure cyclopropanes. Thiourea, which is an odorless and cheap reagent, provides a C[double bond, length as m-dash]S double bond, serves as an amino source, and functions as a decarbalkoxylation reagent in this reaction. Preliminary mechanistic studies demonstrate that the reaction undergoes a sequential [3+2] cycloaddition/deamination/decarboxylation process.

Graphical abstract: Thiourea participation in [3+2] cycloaddition with donor–acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes

Back to tab navigation

Supplementary files

Publication details

The article was received on 03 Dec 2018, accepted on 07 Jan 2019 and first published on 07 Jan 2019


Article type: Communication
DOI: 10.1039/C8CC09595G
Citation: Chem. Commun., 2019, Advance Article
  •   Request permissions

    Thiourea participation in [3+2] cycloaddition with donor–acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes

    M. Xie, G. Zhao, T. Qin, Y. Suo, G. Qu and H. Guo, Chem. Commun., 2019, Advance Article , DOI: 10.1039/C8CC09595G

Search articles by author

Spotlight

Advertisements