A METAL FREE PROCESS FOR THE PREPARATION OF ALPHA-SUBSTITUTED CARBONYL COMPOUNDS FROM ALKENES
The present invention discloses a novel metal free process for the regioselective synthesis of α-substituted carbonyl compounds of formula I from alkene, X is selected from the following compounds (A, B).
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Page/Page column 15-16; 20
(2017/06/19)
Regioselective oxo-amination of alkenes and enol ethers with N-bromosuccinimide-dimethyl sulfoxide combination: A facile synthesis of α-amino-ketones and esters
An unprecedented conversion of alkenes and enol ethers to the corresponding α-imido carbonyl compounds with excellent regioselectivity and yields has been developed. This oxo-amination process employs readily available N-bromosuccinimide (NBS) and secondary amines as N-sources and dimethyl sulfoxide (DMSO) as the oxidant and also leads to the production of amino alcohols in a single step on reduction, thus broadening the scope of this operationally simple reaction. For the first time, the formation of reactive Me2S+-O-Br species generated by the interaction of NBS with DMSO has been proven.
Synthesis of cyclic acylated enamino esters from enol lactones, 4-keto amides, and 5-hydroxy lactams
Enol lactones react with an amine to give either a keto amide or a hydroxy lactam under mild conditions. Subsequent dehydration with p-toluenesulfonic acid (PTSA) gives a cyclic acylated enamino ester in good yield. The key prostaglandin analog precursor 18 and the gly-gly dipeptide analogs 26a and 26b were prepared using the reported conditions. Acetylation of the chloro hydroxy lactam 31, prepared from the chloro enol lactones 29, followed by elimination of acetic acid gave the chloro acylated enamino esters 28.
Abell,Oldham,Taylor
p. 1214 - 1220
(2007/10/02)
A practial method for N-alkylation of succinimide and glutarimide
Succinimide and glutarimide are N-alkylated in high yield using primary chlorides, bromides or tosylates under solid-liquid PTC conditions (K2CO3, benzene or toluene at reflux, 1percent 18-C-6).Addition of 0.1 eq of KI increases the rate of the reaction for less reactive halides such as 2-bromobutane.Keywords: imide / phase transfer catalysis / N-alkylation
Gesson, J. P.,Jacquesy, J. C.,Rambaud, D.
p. 227 - 231
(2007/10/02)
REACTIVITY OF IMINOPHOSPHORANES TOWARDS SOME SYMMETRICAL DICARBONYL DICHLORIDES : SYNTHESES AND MECHANISMS
In situ generated iminophosphoranes 1 react with dicarbonyl dihalides 2a-b and 3a-c to give known or new nitrogen heterocycles.The proposed mechanisms involve elimination of either triphenyl-phosphine oxide or dichlorotriphenylphosphorane depending upon both the iminophosphorane and the dicarbonyl compound.
Aubert, Thierry,Farnier, Michel,Guilard, Roger
p. 53 - 60
(2007/10/02)
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