Thiourea participation in [3+2] cycloaddition with donor–acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes?
Chemical Communications Pub Date: 2019-01-07 DOI: 10.1039/C8CC09595G
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]](https://www.rsc.org/images/entities/char_e001.gif)
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](http://scimg.chem960.com/usr/1/C8CC09595G.jpg)
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Journal Name：Chemical Communications
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CAS no.: 89640-58-4
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