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Thiourea participation in [3+2] cycloaddition with donor-acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes.
- Source :
-
Chemical communications (Cambridge, England) [Chem Commun (Camb)] 2019 Jan 31; Vol. 55 (11), pp. 1580-1583. - Publication Year :
- 2019
-
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.
Details
- Language :
- English
- ISSN :
- 1364-548X
- Volume :
- 55
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- Chemical communications (Cambridge, England)
- Publication Type :
- Academic Journal
- Accession number :
- 30652697
- Full Text :
- https://doi.org/10.1039/c8cc09595g