104787-95-3Relevant academic research and scientific papers
Stereo- and Chemodivergent NHC-Promoted Functionalisation of Arylalkylketenes with Chloral
Douglas, James J.,Churchill, Gwydion,Slawin, Alexandra M. Z.,Fox, David J.,Smith, Andrew D.
, p. 16354 - 16358 (2015)
Stereo- and chemodivergent enantioselective reaction pathways are observed upon treatment of alkylarylketenes and trichloroacetaldehyde (chloral) with N-heterocyclic carbenes, giving selectively either β-lactones (up to 88:12 dr, up to 94% ee) or α-chloroesters (up to 94% ee). Either 2-arylsubstitution or an α-branched iPr alkyl substituent within the ketene favours the chlorination pathway, allowing chloral to be used as an electrophilic chlorinating reagent in asymmetric catalysis.
Enantioselective nucleophilic catalysis: The synthesis of aza-β-lactams through [2+2] cycloadditions of ketenes with azo compounds
Berlin, Jacob M.,Fu, Gregory C.
supporting information; experimental part, p. 7048 - 7050 (2009/04/07)
(Chemical Equation Presented) Get ready for take off: A planar-chiral derivative of 4-pyrrolidinopyridine (1) mediates the title transformation (see scheme) in a convergent manner with good enantioselectivity, thus giving the first catalytic asymmetric synthesis of aza-β-lactams.
