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Pure Appl. Chem., 1988, Vol. 60, No. 11, pp. 1689-1698

http://dx.doi.org/10.1351/pac198860111689

Asymmetric synthesis via nor-ephedrine derived 2-alkenyloxazolidines

C. Scolastico

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  • Zhang Junqing, Xiao Yuanjing, Zhang Junliang: Nickel-Catalyzed Annulation of Donor-Acceptor Oxiranes with Imines: Diastereoselective Access to Highly Substituted 2,4-trans -Oxazolidines. Adv. Synth. Catal. 2013, 355, 2793. <http://dx.doi.org/10.1002/adsc.201300449>
  • Pearson Anthony J., Kwak Yoonhyun: A new method for stereoselective oxidation of chiral 2-pyrrolidino-1-ethanol derivatives to oxazolopyrrolidines using trimethylamine-N-oxide in the presence of iron carbonyls. Tetrahetron Lett 2005, 46, 3407. <http://dx.doi.org/10.1016/j.tetlet.2005.03.101>
  • Andrés José M., Herráiz-Sierra Ignacio, Pedrosa Rafael, Pérez-Encabo Alfonso: A Simple Stereoselective Synthesis of Enantiopure 2-Substituted Pyrrolidines and Piperidines from Chiral (R)-Phenylglycinol-Derived Bicyclic 1,3-Oxazolidines. Eur J Org Chem 2000, 2000, 1719. <http://dx.doi.org/10.1002/(SICI)1099-0690(200005)2000:9<1719::AID-EJOC1719>3.0.CO;2-R>
  • Bernardinelli Gérald, Fernandez Daniel, Gosmini Romain, Meier Peter, Ripa Alberto, Schüpfer Patrick, Treptow Björn, Kündig E. Peter: α-t-butyl- and α-i-propyl-ortho-hydroxybenzylamines: Racemic synthesis/resolution and asymmetric synthesis. Chirality 2000, 12, 529. <http://dx.doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<529::AID-CHIR41>3.0.CO;2-3>
  • Bolm Carsten, Chuang Tsung-Hsun, Raabe Gerhard, Fang Jim-Min: Simple Synthesis of Enantiomerically Pure C2-Symmetric Bisoxazolidines from Amino Alcohols and Formaldehyde. Synth Common 1999, 29, 43. <http://dx.doi.org/10.1080/00397919908085733>
  • Yli-Kauhaluoma Jari T., Harwig Curtis W., Wentworth Paul, Janda Kim D.: Unexpected 1,3-oxazolidine formation in the attempted oxidation of N-aryl-N-methyl substituted β-amino alcohols using pyridinium dichromate. Tetrahetron Lett 1998, 39, 2269. <http://dx.doi.org/10.1016/S0040-4039(98)00289-5>
  • García-Valverde María, Pedrosa Rafael, Vicente Martina, García-Granda S., Gutiérrez-Rodríguez A.: A diastereoselective approach to enantiopure 3-substituted pyrrolidines from masked lithium homoenolates derived from norephedrine. Tetrahedron 1996, 52, 10761. <http://dx.doi.org/10.1016/0040-4020(96)00598-4>
  • Polyak Felix, Dorofeeva Tatiana, Zelchans Gunars, Shustov Gennady: Regio- and stereoselectivity of the formation of 1,3-oxazolidines in the reaction of l-ephedrine with phenylglyoxal. Unexpected rearrangement of 2-benzoyl-3,4-dimethyl-5-phenyl-1,3-oxazolidine to 4,5-dimethyl-3,6-diphenylmorpholin-2-one. Tetrahetron Lett 1996, 37, 8223. <http://dx.doi.org/10.1016/0040-4039(96)01873-4>
  • Agami Claude, Couty François, Lequesne Christelle: N-Boc 2-Acyloxazolidines: Useful precursors to enantiopure 1,2-diols via highly diastereoselective nucleophilic additions. Tetrahedron 1995, 51, 4043. <http://dx.doi.org/10.1016/0040-4020(95)00145-X>
  • Harder Timm, Löhl Thorsten, Bolte Michael, Wagner Kerstin, Hoppe Dieter: Enantioselective synthesis of α-branched α-hydroxy ketones via chiral N-sulfonyl-2-alkyl-2-cyano-1,3-oxazolidines. Tetrahetron Lett 1994, 35, 7365. <http://dx.doi.org/10.1016/0040-4039(94)85315-0>
  • Agami Claude, Couty François, Lequesne Christelle: Asymmetric synthesis of homochiral 1,2-diols via N-boc oxazolidines. Tetrahetron Lett 1994, 35, 3309. <http://dx.doi.org/10.1016/S0040-4039(00)76893-6>
  • Hussain Abid, Wyatt Peter B: 2-(penta-1,3-dienyl)oxazolidines: synthesis of hydroxylated piperidines by a stereoselective diels-alder Reaction. Tetrahedron 1993, 49, 2123. <http://dx.doi.org/10.1016/S0040-4020(01)86312-2>
  • Andrés Celia, Delgado Manuel, Pedrosa Rafael, Rodríguez Raquel: A novel highly diastereoselective synthesis of cyano ethers by regioselective ring opening of chiral oxazolidinium methiodides with sodium cyanide. Tetrahetron Lett 1993, 34, 8325. <http://dx.doi.org/10.1016/S0040-4039(00)61422-3>
  • Conde-Frieboes Kilian, Hoppe Dieter: Norpseudoephedrine-derived 2-methoxy-3-sulfonyl-1,3-oxazolidines: Chiral, highly diastereoselective formyl cation equivalents. Tetrahedron 1992, 48, 6011. <http://dx.doi.org/10.1016/S0040-4020(01)89849-5>
  • Andrés Celia, González Alfonso, Pedrosa Rafael, Pérez-Encabo Alfonso, García-Granda Santiago, Salvadó M.A., Gómez-Beltrán Fermín: A new chiral glycine synthon. Synthesis, x-ray structure of (−).(2S,4R)-2-ethoxycarbonyl-4-phenyl-1,3-oxazolidine and diastereoselective nucleophilic ring opening to (R)-ethyl α-amino carboxylates. Tetrahetron Lett 1992, 33, 4743. <http://dx.doi.org/10.1016/S0040-4039(00)61274-1>
  • Andrés Celia, González Alfonso, Pedrosa Rafael, Pérez-Encabo Alfonso: Stereoselective ring opening of chiral oxazolidines by reformatsky reagents: an enantioselective entry to β-amino esters. Tetrahetron Lett 1992, 33, 2895. <http://dx.doi.org/10.1016/S0040-4039(00)78889-7>
  • Hoppe Inga, Hoppe Dieter, Herbst-Irmer Regine, Egert Ernst: Asymmetric aldol addition reactions of a chiral 3-sulfonyl-1,3-oxazolidine-masked lithium 2-formylcyclohexanone enolate. Tetrahetron Lett 1990, 31, 6859. <http://dx.doi.org/10.1016/S0040-4039(00)97190-9>