Organocatalytic atropo- and E/Z-selective Michael addition reaction of ynones with α-amido sulfones as sulfone-type nucleophile. Issue 4 (8th January 2019)

• Record Type: Journal Article
• Authors: Zhang, Nan; He, Tingting; Liu, Yidong; Li, Shan; Tan, Yu; Peng, Lei; Li, Dongmei; Shan, Chunhui; Yan, Hailong
• Is Part Of: Organic chemistry frontiers. Volume 6:Issue 4(2019)
• Page Start: 451
• Page End: 455
• Publication Date: 2019-01-08
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c8qo01241e
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : We describe herein the first enantioselective organocatalytic Michael addition reaction of α-amido sulfones to ynones to access axially chiral styrenes. Abstract : We describe herein the first enantioselective organocatalytic Michael addition reaction of α-amido sulfones to ynones to access axially chiral styrenes. Sulfone-containing axially chiral styrene compounds were constructed with excellent enantioselectivity and almost complete E / Z -selectivity (up to 97% ee, >20 : 1 E / Z ) in the presence of an easily accessible cinchona-alkaloid-derived multiple hydrogen-bonding catalyst. The enantioenriched sulfone-containing products were used as precursors for further transformations without any loss of the ee value. The equilibration process of this transformation was monitored by 1 H NMR spectroscopy.