Issue 11, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
03 12 2018
Accepted
07 1 2019
First published
07 1 2019

Chem. Commun., 2019,55, 1580-1583

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, 55, 1580 DOI: 10.1039/C8CC09595G

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