2832-16-8Relevant articles and documents
Phosphoramidites are efficient, green organocatalysts for the Michael reaction. Mechanistic insights into the phosphorus-catalyzed Michael reaction of alkynones and implications for asymmetric catalysis
Grossman, Robert B.,Comesse, Sebastien,Rasne, Ravindra M.,Hattori, Kazuyuki,Delong, Matthew N.
, p. 871 - 874 (2003)
Hexamethylphosphorous triamide (HMPT) and other phosphoramidites and phosphites have been found to be efficient catalysts for the Michael reaction of alkenones and alkynones with malonates, α-cyano esters, β-keto esters, and nitro compounds. The relativel
Intermolecular domino Michael/aldol reactions of α,β-unsaturated esters, aromatic aldehydes, and various nucleophiles promoted with a catalytic amount of a guanidine base in DMSO
Matsuo, Jun-ichi,Morita, Shunya,Yoshimura, Tomoyuki
, (2021/07/28)
In DMSO, a catalytic amount of Barton's base (2-t-butyl-1,1,3,3-tetramethylguanidine, BTMG) effectively catalyzed intermolecular three-component reactions of α,β-unsaturated esters, aldehydes, and carbon-, sulfur-, or nitrogen-pronucleophiles to give three-component addition products with the formation of two new σ-bonds: pronucleophiles and aldehydes reacted with α,β-unsaturated esters at their β-positions and α-positions, respectively. Mechanism studies suggested that these reactions proceeded by the first intermolecular Michael addition of anionic nucleophiles that were formed from pronucleophiles with a catalytic amount of BTMG, followed by intermolecular aldol reactions of transient ester enolates even in the presence of more than stoichiometric amounts of acidic pronucleophiles. High nucleophilicity over Br?nsted basicity of transient enolates in polar solvents was observed for transient ester enolates rather than ketone enolates.
Stereoselective aza-Henry reaction of chiral tert-butanesulfinyl imines with methyl or ethyl 4-nitrobutanoate: Easy access to enantioenriched 6-substituted piperidine-2,5-diones
Garca-Muoz, M. Jess,Foubelo, Francisco,Yus, Miguel
, p. 1419 - 1432 (2015/06/02)
The base-catalyzed addition of 4-nitrobutanoates 6 to N-tert-butanesulfinyl imines 8 under solvent-free reaction conditions proceeded with high face diastereoselectivity. The resulting β-nitroamine derivatives 9 were easily transformed into 6-substituted piperidine-2,5-diones 11 upon removal of the sulfinyl group with concomitant δ-lactam formation and functional group transformation under Nef reaction conditions.
Base-catalysed intramolecular hydroamination of vinyl sulfiies
Quinet, Coralie,Sampoux, Laetitia,Marko, Istvan E.
supporting information; experimental part, p. 1806 - 1811 (2009/09/06)
Small amounts of n-butyllithium catalyse the highly efficient hydroamination of a large variety of vinyl sulfides. This novel methodology offers an easy access to a wide range of nitrogen heterocycles, including simple pyrrolidines and piperidines, as well as more complex bicyclic compounds. Subsequent transformations of the sulfur group led to the formation of functionalised alkaloid-like substructures. Wiley-VCH Verlag GmbH & Co. KGaA.