Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart ˙ New York Asymmetric Synthesis of 1,2-anti-Disubstituted Taurine Derivatives Dieter Enders*, Dirk Iffland, Gerhard RaabeInstitute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, GermanyFax: +49(241)8092127; e-Mail: enders@rwth-aachen.de; Recommend Article Abstract Buy Article All articles of this category Abstract An efficient asymmetric synthesis of anti-1,2-disubstituted taurine derivatives through nucleophilic addition of phenylmethanesulfonate to various N-acylimines in the presence of 1,2:5,6-di-O-isopropylidene-α-d-allofuranose as a chiral auxiliary is described. The taurine derivatives were obtained in three steps with good overall yields (36-61%) and excellent enantiomeric excesses (83-98%). The diastereomeric excesses of 15-91% could be improved to 90-98% by column chromatography or recrystallization. The relative and absolute configurations of the products were determined by means of an X-ray crystal structure analysis. Key words taurine - asymmetric synthesis - sugar auxiliary - N-acylimines - α-amido sulfones - chiral auxiliary Full Text References References 1 Kalir A. Kalir HH. In The Chemistry of Sulfonic Acids, Esters and their Derivatives Patai S. Rappoport Z. Wiley; New York: 1991. p.767 2 Huxtable RJ. Physiol. Rev. 1992, 72: 101 3 Xu J. Xu S. Synthesis 2004, 276 4 Xu J. Xu S. Zhang QH. Heteroat. Chem. 2005, 16: 466 5 Huang J. Wang F. Du DM. Xu J. Synthesis 2005, 2122 6a Higashiura K. Morino H. Matsuura H. Toyomaki Y. Ienaga K. J. Chem. Soc., Perkin Trans. 1 1989, 6b Higashiura K. Ienaga K. J. Org. Chem. 1992, 57: 764 6c Moree WJ. van der Marel GA. Liskamp RMJ. Tetrahedron Lett. 1992, 33: 6389 6d Moree WJ. van der Marel GA. Liskamp RMJ. J. Org. Chem. 1995, 60: 5157 6e Braghiroli D. Di Bella M. Tetrahedron: Asymmetry 1996, 7: 2145 6f Braghiroli D. Di Bella M. Tetrahedron Lett. 1996, 37: 7319 6g Monnee MCF. Marijne MF. Brouwer AJ. Liskamp RMJ. Tetrahedron Lett. 2000, 41: 7991 7 Xu J. Tetrahedron: Asymmetry 2002, 13: 1129 8 Gold MH. Skebelsky M. Lang G. J. Org. Chem. 1951, 16: 1500 9 Huang J. Du D.-M. Xu J. Synthesis 2006, 315 10 Cordero FM. Cacciarini M. Machetti F. De Sarlo F. Eur. J. Org. Chem. 2002, 1407 12a Koller W. Linkies A. Rehling H. Reuschling D. Tetrahedron Lett. 1983, 24: 2131 12b Hu LB. Zhu H. Du DM. Xu JX. J. Org. Chem. 2007, 72: 4543 12 Wang B. Zhang W. Zhang L. Du D.-M. Liu G. Xu J. Eur. J. Org. Chem. 2008, 350 14a Enders D. Wallert S. Synlett 2002, 304 14b Enders D. Wallert S. Runsink J. Synthesis 2003, 1856 15a Enders D. Vignola N. Berner OM. Angew. Chem. Int. Ed. 2002, 41: 109 ; Angew. Chem. 2002, 114, 116 15b Enders D. Berner OM. Vignola N. Chem. Commun. 2001, 2498 15c Enders D. Berner OM. Vignola N. Harnying W. Synthesis 2002, 1945 16a Enders D. Harnying W. Vignola N. Synlett 2002, 1727 16b Enders D. Harnying W. Vignola N. Eur. J. Org. Chem. 2003, 20: 3939 16 Enders D. Harnying W. Synthesis 2004, 2910 18a Enders D. Harnying W. ARKIVOC 2004, (ii): 181 ; available online at www.arkat-usa.org 18b Enders D. Harnying W. Raabe G. Synthesis 2004, 590 18c Enders D. Iffland D. Synthesis 2007, 1837 18 Enders D. Adelbrecht J.-C. Harnying W. Synthesis 2005, 2962 19 Harnying W. Kitisriworaphan W. Pohmakotr M. Enders D. Synlett 2007, 2529 20 CCDC 713539 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from www.ccdc.cam.ac.uk/data_request/cif or by contacting the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK: fax: +44(1223)336033.
