Stereochemical aspects and the synthetic scope of the SHi at the sulfur atom. Preparation of enantiopure 3-substituted 2,3-dihydro-1,2-benzoisothiazole 1-oxides and 1,1-dioxides
作者： José A. Fernández-Salas , M. Mercedes Rodríguez-Fernández , M. Carmen Maestro , José L. García-Ruano
DOI: 10.1039/C4CC01831A
关键词:
摘要: Intramolecular homolytic substitution (SHi) on the sulfur atom at acyclic N-(o-bromobenzyl)sulfinamides takes place with a complete inversion of configuration and provides an excellent tool to connect N-tert-butanesulfinylimines enantiopure 3-substituted benzo-fused sulfinamides (1,2-benzoisothiazoline 1-oxides) related pharmacologically relevant sulfonamides.
rsc.org
core.ac.uk
sci-hub.se 参考文章(24)
Chris H. Senanayake, Zhengxu Han, Dhileepkumar Krishnamurthy, Synthesis and Use of Chiral Sulfinamides Organosulfur Chemistry in Asymmetric Synthesis. pp. 233- 264 ,(2009) , 10.1002/9783527623235.CH7
Aurore Beaume, Christine Courillon, Etienne Derat, Max Malacria, Unprecedented aromatic homolytic substitutions and cyclization of amide-iminyl radicals: experimental and theoretical study. Chemistry: A European Journal. ,vol. 14, pp. 1238- 1252 ,(2008) , 10.1002/CHEM.200700884
Chang-Bin Yu, Kao Gao, Duo-Sheng Wang, Lei Shi, Yong-Gui Zhou, Enantioselective Pd-catalyzed hydrogenation of enesulfonamides Chemical Communications. ,vol. 47, pp. 5052- 5054 ,(2011) , 10.1039/C1CC10313J
Chang-Bin Yu, Da-Wei Wang, Yong-Gui Zhou, Highly Enantioselective Synthesis of Sultams via Pd-Catalyzed Hydrogenation Journal of Organic Chemistry. ,vol. 74, pp. 5633- 5635 ,(2009) , 10.1021/JO900790K
Heather M. Aitken, Amber N. Hancock, Carl H. Schiesser, Understanding (the lack of) homolytic substitution chemistry of sulfones. Chemical Communications. ,vol. 48, pp. 8326- 8328 ,(2012) , 10.1039/C2CC33856D
Sara H. Kyne, Heather M. Aitken, Carl H. Schiesser, Emmanuel Lacôte, Max Malacria, Cyril Ollivier, Louis Fensterbank, Intramolecular homolytic substitution of sulfinates and sulfinamides – a computational study Organic & Biomolecular Chemistry. ,vol. 9, pp. 3331- 3337 ,(2011) , 10.1039/C1OB05043E
Niklas Plobeck, David Powell, Asymmetric synthesis of diarylmethylamines by diastereoselective addition of organometallic reagents to chiral N-tert-butanesulfinimines: switchover of diastereofacial selectivity Tetrahedron: Asymmetry. ,vol. 13, pp. 303- 310 ,(2002) , 10.1016/S0957-4166(02)00099-X
Elise M. Rochette, William Lewis, Al G. Dossetter, Robert A. Stockman, Highly diastereoselective radical cyclisations of chiral sulfinimines Chemical Communications. ,vol. 49, pp. 9395- 9397 ,(2013) , 10.1039/C3CC45452E
L. Nathan Tumey, Michael J. Robarge, Elizabeth Gleason, Jianping Song, Steven M. Murphy, George Ekema, Chris Doucette, Doug Hanniford, Marc Palmer, Gary Pawlowski, Joel Danzig, Margaret Loftus, Karen Hunady, Bruce Sherf, Robert W. Mays, Alain Stricker-Krongrad, Kurt R. Brunden, Youssef L. Bennani, John J. Harrington, 3-Indolyl sultams as selective CRTh2 antagonists Bioorganic & Medicinal Chemistry Letters. ,vol. 20, pp. 3287- 3290 ,(2010) , 10.1016/J.BMCL.2010.04.046
MaryAnn T. Robak, Melissa A. Herbage, Jonathan A. Ellman, Synthesis and Applications of tert-Butanesulfinamide Chemical Reviews. ,vol. 110, pp. 3600- 3740 ,(2010) , 10.1021/CR900382T