550346-57-1Relevant academic research and scientific papers
Flexible, phase-transfer catalyzed approaches to 4-substituted prolines
Johnston, Heather J.,McWhinnie, Fergus S.,Landi, Felicetta,Hulme, Alison N.
supporting information, p. 4778 - 4781 (2015/04/27)
A range of 4-substituted prolines can be rapidly synthesized from a protected glycine Schiff base in only four steps and in 27-55% overall yield. Phase transfer catalysis allows direct access to both enantiomeric series, and the relative stereochemistry at the 4-position is readily controlled (>10:1 dr) through the choice of hydrogenation conditions.
Total synthesis of (±)-manzacidin D
Drouin, Christian,Woo, Jacqueline C.S.,MacKay, D. Bruce,Lavigne, Roch M.A.
, p. 7197 - 7199 (2007/10/03)
We report herein the first total synthesis of the alkaloid manzacidin D, in 11 steps and 16% overall yield from commercially available glycine tert-butyl ester hydrochloride. Our synthesis demonstrates for the first time in a total synthesis the utility of two different methodologies. A highly diastereoselective iodocyclization of an olefinic isothiourea is used to induce stereocontrol at the quaternary centre, and to form the heterocyclic core. Conversion of a thiourea to the requisite formamidine is achieved in good yield using our modified procedure.
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.
Identification of a highly effective asymmetric phase-transfer catalyst derived from α-methylnaphthylamine
Lygo, Barry,Allbutt, Bryan,James, S. Russell
, p. 5629 - 5632 (2007/10/03)
A library of quaternary ammonium salts has been generated via reaction of simple chiral amines with a series of conformationally dynamic biphenyl units. Screening of this library against the alkylation of a glycine imine has led to the identification of a highly effective asymmetric phase-transfer catalyst derived from α-methylnaphthylamine.
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
