Thiourea participation in [3+2] cycloaddition with donor–acceptor cyclopropanes: a domino process to 2-amino-dihydrothiophenes. Issue 11 (17th January 2019)

• Record Type: Journal Article
• Authors: Xie, Ming-Sheng; Zhao, Guo-Feng; Qin, Tao; Suo, Yong-Bo; Qu, Gui-Rong; Guo, Hai-Ming
• Is Part Of: Chemical communications. Volume 55:Issue 11(2019)
• Page Start: 1580
• Page End: 1583
• Publication Date: 2019-01-17
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc09595g
• Languages: English
• ISSNs: 1359-7345

Abstract

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. 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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.