39837-35-9Relevant articles and documents
Fe-catalyzed allylic C-C-bond activation: Vinylcyclopropanes as versatile a1,a3,d5-synthons in traceless allylic substitutions and [3 + 2]-cycloadditions
Dieskau, Andre P.,Holzwarth, Michael S.,Plietker, Bernd
, p. 5048 - 5051 (2012/05/05)
The low-valent iron complex Bu4N[Fe(CO)3(NO)] (TBAFe) catalyzes the allylic C-C-bond activation of electron-poor vinyl cyclopropanes to generate synthetically useful a1,a3,d5-synthons which are prone to undergo multiple consecutive reactions. The versatility of this approach is demonstrated by a traceless allylic substitution and a formal [3 + 2] cycloaddition to give either functionalized acyclic products or densely substituted cyclopentanes and pyrrolidines in high yields and regioselectivities.
Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging michael acceptors
Sulzer-Mosse, Sarah,Alexakis, Alexandre,Mareda, Jiri,Bollot, Guillaume,Bernardinelli, Gerald,Filinchuk, Yaroslav
supporting information; experimental part, p. 3204 - 3220 (2009/12/03)
Chiral amines with a pyrrolidine framework catalyze the enantioselective conjugate addition of a broad range of aldehydes to various vinyl sulfones and vinyl phosphonates in high yields and with enantioselectivities up to >99% ee. This novel process provides synthetically useful chiral γ-gem-sulfonyl or phosphonyl aldehydes which can be widely functionalized with retention of the enantiomeric excess. Mechanistic insights including DFT calculations are explored in detail.
REACTION OF 1,1-BIS(PHENYLSULFONYL)ETHENE WITH AMINES
Bazavova, I. M.,Neplyuev, V. M.,Lozinskii, M. O.
, p. 74 - 77 (2007/10/02)
The reactions of 1,1-bis(phenylsulfonyl)ethene with aliphatic, aromatic, and heterocyclic amines in anhydrous aprotic solvents take place in two directions, depending on the basicity of the amine.They lead to the formation of secondary 1,1-bis(phenylsulfonyl)-ethyl-N-aryl(heteryl)amines as addition products, or to 1,1,3,3-tetrakis(phenylsulfonyl)propane, or to their mixtures.By analysis of the reaction mixtures and identification of the intermediate products a scheme was proposed for the reactions of 1,1-bis(phenylsulfonyl)ethene with amines.