277759-54-3Relevant academic research and scientific papers
A rapid approach to amino-acid derivatives by [2,3]-stevens rearrangement
Arboré, Amélie P.A.,Cane-Honeysett, Daniel J.,Coldham, Iain,Middleton, Mark L.
, p. 236 - 238 (2000)
Allylation of amino-acid esters gives rise to intermediate quaternary ammonium salts, which undergo proton abstraction to give ylides and [2,3]- sigmatropic rearrangement. The resulting α-amino-acid derivatives can be subjected to N-deallylation to provid
Substrate stereocontrol in the intramolecular organocatalyzed tsuji-trost reaction: Enantioselective synthesis of allokainates
Vulovic, Bojan,Gruden-Pavlovic, Maja,Matovic, Radomir,Saicic, Radomir N.
supporting information, p. 34 - 37 (2014/01/23)
Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.
Diastereoselective isothiourea iodocyclization for manzacidin synthesis
Woo, Jacqueline C.S.,MacKay, D. Bruce
, p. 2881 - 2883 (2007/10/03)
We have devised a novel strategy for the total synthesis of the manzacidins. Our approach utilizes an isothiourea iodocyclization strategy to directly form the heterocyclic core, and in the process induce stereoselectivity at the quaternary center. We have found that cyclization can be achieved using an isothiourea as the nucleophilic partner. Cyclization proceeds smoothly using IBr at low temperature, affording an advanced intermediate along our proposed route to manzacidin A in 92% yield. We have demonstrated the scope of the reaction by preparing several cyclic isothioureas, including an intermediate on our proposed route for the synthesis of manzacidin D.
Thiol-Mediated Free Radical Cyclization of Alkenyl and Alkynyl Isocyanides
Bachi, Mario D.,Balanov, Anna,Bar-Ner, Nira
, p. 7752 - 7758 (2007/10/02)
Thiol-mediated free radical cyclizations of but-3-enyl and but-3-ynyl isocyanides of types 6-8 give new access to 3,5-disubstituted 2-(alkyl- and 2-(arylthio)pyrrolines 11, 12, and 18.When 2-mercaptoethanol is used with the same isocyanides the reaction r
