2433-57-0Relevant articles and documents
Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones
Boylan, Amy,Li, Jian-Yuan,Lundy, Brian J.,May, Jeremy A.,Nguyen, Thien S.,Sundstrom, Sasha,Vallakati, Ravikrishna
, (2021/06/16)
Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.
Isothiourea-catalysed enantioselective pyrrolizine synthesis: Synthetic and computational studies
Stark, Daniel G.,Williamson, Patrick,Gayner, Emma R.,Musolino, Stefania F.,Kerr, Ryan W. F.,Taylor, James E.,Slawin, Alexandra M. Z.,O'Riordan, Timothy J. C.,Macgregor, Stuart A.,Smith, Andrew D.
supporting information, p. 8957 - 8965 (2016/10/07)
The catalytic enantioselective synthesis of a range of cis-pyrrolizine carboxylate derivatives with outstanding stereocontrol (14 examples, >95:5 dr, >98:2 er) through an isothiourea-catalyzed intramolecular Michael addition-lactonisation and ring-opening
Electron deficiency of aldehydes controls the pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes and ketones in water
Chimni, Swapandeep Singh,Mahajan, Dinesh
, p. 5019 - 5025 (2007/10/03)
A synthetically useful pyrrolidine catalyzed direct cross-aldol reaction of aromatic/heterocyclic aldehydes with ketones in water affords the aldol addition product in up to 93% yield. Electrophilicity of the aldehydes controls the course of the reaction.