90867-76-8Relevant academic research and scientific papers
Enantioselective photoredox catalysis enabled by proton-coupled electron transfer: Development of an asymmetric aza-pinacol cyclization
Rono, Lydia J.,Yayla, Hatice G.,Wang, David Y.,Armstrong, Michael F.,Knowles, Robert R.
supporting information, p. 17735 - 17738 (2014/01/06)
The first highly enantioselective catalytic protocol for the reductive coupling of ketones and hydrazones is reported. These reactions proceed through neutral ketyl radical intermediates generated via a concerted proton-coupled electron transfer (PCET) event jointly mediated by a chiral phosphoric acid catalyst and the photoredox catalyst Ir(ppy)2(dtbpy)PF6. Remarkably, these neutral ketyl radicals appear to remain H-bonded to the chiral conjugate base of the Bronsted acid during the course of a subsequent C-C bond-forming step, furnishing syn 1,2-amino alcohol derivatives with excellent levels of diastereo- and enantioselectivity. This work provides the first demonstration of the feasibility and potential benefits of concerted PCET activation in asymmetric catalysis.
Arylation and vinylation of alkenes based on unusual sequential semipinacol rearrangement/Grob fragmentation of allylic alcohols
Yuan, Dao-Yi,Tu, Yong-Qiang,Fan, Chun-An
, p. 7797 - 7799 (2008/12/22)
(Chemical Equation Presented) Alkenes can be stereoselectively arylated and vinylated without transition-metal catalyst under mild conditions through an interesting NBS-promoted semipinacol rearrangement and a subsequent unusual NaOH-mediated Grob fragmentation.
Synthesis of α-Hydroxy Carbonyl Compounds (Acyloins): Direct Oxidation of Enolates Using 2-Sulfonyloxaziridines
Davis, Franklin A.,Vishwakarma, Lal C.,Billmers, Joanne M.,Finn, John
, p. 3241 - 3243 (2007/10/02)
Direct oxidation of ketone and ester enolates, using 2-sulfonyloxaziridine 1, affords α-hydroxy carbonyl compounds (acyloins) in high yield with excellent stereoselectivity.
