Cinchona Alkaloids as Organocatalysts in Enantioselective Halofunctionalization of Alkenes and Alkynes. Issue 4 (1st April 2014)

• Record Type: Journal Article
• Authors: Zheng, Suqing; Schienebeck, Casi M.; Zhang, Wei; Wang, Hao‐Yuan; Tang, Weiping
• Is Part Of: Asian journal of organic chemistry. Volume 3:Issue 4(2014:Apr.)
• Page Start: 366
• Page End: 376
• Publication Date: 2014-04-01
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201400030
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Naturally occurring cinchona alkaloids include quinine, quinidine, cinchonine, and cinchonidine. Many of their derivatives are also readily available. This Focus Review summarizes recent applications of cinchona alkaloid derivatives, an important class of organocatalysts, in enantioselective halofunctionalization of alkenes and alkynes. Most successful examples in this area are intramolecular halofunctionalizations, where the nucleophile is tethered with the alkene or alkyne substrate. Only a few catalytic enantioselective intermolecular halofunctionalization of alkenes have been realized. Dimeric cinchona alkaloids are the most frequently used catalysts in asymmetric halofunctionalizations. Most other catalysts have an appended functional group on the C9 position of the cinchona alkaloids. These functional groups include (thio)urea, thiocarbamate, and sulfonamides.</p> </abstract>