Diethyl (cyanofluoromethyl)phosphonate: Application in catalytic enantioselective Michael additions. (3rd June 2017)

• Record Type: Journal Article
• Authors: Jászay, Zsuzsa; Tódor, István; Rapi, Zsolt; Bakó, Péter; Petneházy, Imre; Tőke, László
• Is Part Of: Phosphorus, sulfur, and silicon and the related elements. Volume 192:Number 6(2017)
• Page Start: 659
• Page End: 664
• Publication Date: 2017-06-03
• Subjects: Fluorophosphonates -- catalytic enantioselective Michael additions -- sugar-based crown ethers; Sulfur compounds -- Periodicals; Organosulfur compounds -- Periodicals; Phosphorus compounds -- Periodicals; Organophosphorus compounds -- Periodicals; Silicon compounds -- Periodicals; Organosilicon compounds -- Periodicals; 546
• DOI: 10.1080/10426507.2017.1311334
• Languages: English
• ISSNs: 1042-6507

Abstract

GRAPHICAL ABSTRACT: ABSTRACT: Three types of chiral catalysts: a chincona-based squaramide, TADDOL and a group of sugar-based crown ethers were applied to the asymmetric Michael addition of diethyl (cyanofluoromethyl)phosphonate to diverse Michael acceptors. Two of the crown ether catalysts resulted in high yields and enantioselectivities with trans -β-nitostyrene as in case of the chincona-based squaramide catalyst the yield was low with high enantioselectivity. TADDOL proved to be active, but less selective in the Michael addition.