- Enantioselective organocatalytic conjugate addition of aldehydes to vinyl sulfones and vinyl phosphonates as challenging michael acceptors
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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.
- Sulzer-Mosse, Sarah,Alexakis, Alexandre,Mareda, Jiri,Bollot, Guillaume,Bernardinelli, Gerald,Filinchuk, Yaroslav
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supporting information; experimental part
p. 3204 - 3220
(2009/12/03)
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- Organocatalytic addition on l,2-bis(sulfone)vinylenes leading to an unprecedented rearrangement
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A study was conducted to demonstrate the use of 1,2-bis(sulfone)vinylenes in enamine catalysis. It was revealed that these sulfones led to a new rearrangement arising from a sulfone shift to the adjacent carbon atom. Investigations also revealed that the use of cheaper (Z)-1,2-bis(sulfone) vinylene lead to full conversion after a short reaction time in dioxane, using H2O as co-catalyst to accelerate the reaction. A careful NMR investigation indicated that the new product was gem-disulfone, which was supported by authentic sample.
- Quintard, Adrien,Alexakis, Alexandre
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supporting information; scheme or table
p. 11109 - 11113
(2010/04/29)
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- THE REACTION BETWEEN PHENYLIODONIUM BIS(PHENYLSULFONYL)METHANIDE AND PYRROLIDINE
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The main product from the title reaction is the enamine N--pyrrolidine, 4.Tetrakis(phenylsulfonyl)propane, 3, is a by-product, when dichloromethane is used; it is formed independently from this solvent and bis(phenylsulfonyl)methane in the presence of pyrrolidine.Key words: Phenyliodonium bis(phenylsulfonyl)methanide, N--pyrrolidine, 1,1,3,3-tetrakis(phenylsulfonyl)propane, dichloromethane, pyrrolidine.
- Nikas, Spyros,Rodios, Nestor,Terzis, Aris,Varvoglis, Anastassios
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p. 285 - 288
(2007/10/02)
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- REACTION OF 1,1-BIS(PHENYLSULFONYL)ETHENE WITH AMINES
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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.
- Bazavova, I. M.,Neplyuev, V. M.,Lozinskii, M. O.
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- REACTIONS OF 1,1-BIS(ARYLSULFONYL)ETHENES WITH NUCLEOPHILIC AND ELECTROPHILIC REAGENTS
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The reaction of 1,1-bis(arylsulfonyl)ethenes with nucleophilic reagents (aromatic and heterocyclic thiols, sulfinic acids) leads to the formation of 1,1-bis(arylsulfonyl)-2-aryl(heteryl)-thio(sulfonyl)ethanes.The anions of CH acids (nitromethane, aromatic
- Bazavova, I. M.,Neplyuev, V. M.,Lozinskii, M. O.
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p. 750 - 753
(2007/10/02)
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