Dial-in selection of any of four stereochemical outcomes among two substrates by in situ stereo-reconfiguration of a single ambidextrous catalyst. Issue 4 (27th January 2016)

• Record Type: Journal Article
• Authors: Mortezaei, Shahab; Catarineu, Noelle R.; Canary, James W.
• Is Part Of: Tetrahedron letters. Volume 57:Issue 4(2016)
• Page Start: 459
• Page End: 462
• Publication Date: 2016-01-27
• Subjects: Asymmetric catalysis -- Ambidextrous -- Dynamic -- Helical inversion -- Michael addition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.12.015
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: We provide proof-of-principle that an ambidextrous catalyst is capable of independent, dial-in control of the absolute stereochemistry of two similar nitrostyrene Michael addition reactions by in situ oxidation and reduction of the catalyst. The catalyst is capable of both static and dynamic catalysis modes; in combination both modes allow access to all four possible stereochemical outcomes for the two nitroalkane products in a single process.