Catalytic Asymmetric Synthesis of Esomeprazole by a Titanium Complex with a Hexa-aza-triphenolic Macrocycle Ligand

REFERENCES

• (a) Shin , J. M. ; Munson , K.; Vagin O. ; Sachs , G. Pflugers Arch. Eur. J. Physiol. 2009 , 457 , 609 – 622 ; (b) Robinson , M. Int. J. Clin. Pract. 2005 , 59 , 709 – 715 .
   PubMed Web of Science ®Google Scholar
• Olbe , L. ; Carlsson , E. ; Lindberg , P. Nat. Rev. Drug Discov. 2003 , 2 , 132 – 139 .
   PubMed Web of Science ®Google Scholar
• The Top 25 Best-Selling Drugs of 2013. Available at http://www.genengnews.com/insight-and-intelligenceand153/the-top-25-best-selling-drugs-of-2013/77900053/ .
   Google Scholar
• (a) Pitchen , P. ; Duñach , E. ; Deshmukh , M. N. ; Kagan , H. B. J. Am. Chem. Soc. 1984 , 106 8188 – 8193 ; (b) Pitchen , P. ; Kagan , H. B. ; Tetrahedron Lett. 1984 , 25 , 1049 – 1052 ; (c) Di Furia , F. ; Modena , G. ; Seraglia , R. Synthesis 1984 , 325 – 326 .
   Web of Science ®Google Scholar
• (a) Fernández , I. ; Khiar , N. Chem. Rev. 2003, 103, 3651–3705; (b) Srour , H. ; Le Maux , P. ; Chevance , S. ; Simonneaux , G. Coordin. Chem. Rev. 2013, 257, 3030–3050; (c) Zeng , Q. ; Gao , S. ; Chelashaw , A. K. Mini-Rev. Org. Chem. 2013, 10, 198–206; (d) Romanowski , G. ; Kira , J. ; Wera , M. J. Mol. Cat. A: Chem. 2014, 381, 148–160; (e) Jindal , G. ; Sunoj , R. B. Angew. Chem. Int. Ed. 2014, 53, 4432–4436; (f) Jurok , R. ; Hodacova , J. ; Eigner , V. ; Dvorakova , H. ; Setnicka , V. ; Cibulka , R. Eur. J. Org. Chem. 2013, 7724–7738; (g) Tanaka , K. ; Kubo , K. ; Iida , K. ; Otani , K. ; Murase , T. ; Yanamoto , D. ; Shiro , M. Asian J. Org. Chem. 2013, 2, 1055–1060; (h) O'Mahony , G. E. ; Eccles , K. S. ; Morrison , R. E. ; Ford , A. ; Lawrence , S. E. ; Maguire , A. R. Tetrahedron 2013, 69, 10168–10184; (i) Aydin , A. E. Tetrahedron: Asmmetry 2013, 24, 444–448; (j) Zhu , C. F. ; Chen , X. ; Yang , Z. W. ; Du , X. ; Liu , Y. ; Cui , Y. Chem. Comm. 2013, 49, 7120–7122; (k) Xuan , W. M. ; Ye , C. C. ; Zhang , M. N. ; Chen , Z. J. ; Cui , Y. Chem. Sci. 2013, 4, 3154–3159; (l) Bottoni , A. ; Calvaresi , M. ; Ciogli , A. ; Cosimelli , B. ; Mazzeo , G. ; Pisani , L. ; Severi , E. ; Spinelli , D. ; Superchi , S. Adv. Synth. Catal. 2013, 355, 191–202; (m) Malik , P. ; Chakraborty , D. Tetrahedron Lett. 2012, 53, 5652–5655; (n) Stingl , K. A. ; Weiss , K. M. ; Tsogoeva , S. B. Tetrahedron 2012, 68, 8493–8501; (o) Liao , S. H. ; Coric , I. ; Wang , Q. G. ; List , B. J. Am. Chem. Soc. 2012, 134, 10765–10768; (p) O'Mahony , G. E. ; Ford , A. ; Maguire , A. R. J. Org. Chem. 2012, 77, 3288–3296; (q) Das , S. P. ; Boruah , J. J. ; Chetry , H. ; Islam , N. S. Tetrahedron Lett. 2012, 53, 1163–1168; (r) Liu , Z.-M. ; Zhao , H. ; Li , M.-Q. ; Lan , Y.-B. ; Yao , Q.-B. ; Tao , J.-C. ; Wang , X.-W. Adv. Synth. Catal. 2012, 354, 1012–1022; (s) Newhouse , T. R. ; Li , X. ; Blewett , M. M. ; Whitehead , C. M. C. ; Corey , E. J. J. Am. Chem. Soc. 2012, 134, 17354–17357.
   PubMed Web of Science ®Google Scholar
• (a) Cotton , H. ; Elebring , T. ; Larsson , M. ; Li , L. ; Sörensen , H. ; Unge , S. Tetrahedron: Asymmetry 2000 , 11 , 3819 – 3825 ; (b) Seenivasaperumal , M. ; Federsel , H.-J. ; Ertan , A. ; Szabó , K. J. Chem. Commun. 2007 , 2187 – 2189 ; (c) Seenivasaperumal , M. ; Federsel , H.-J. ; Szabó , K. J. Adv. Synth. Catal. 2009 , 351 , 903 – 919 .
   Web of Science ®Google Scholar
• Che , G. ; Xiang , J. ; Tian , T. ; Huang , Q. ; Cun , L. ; Liao , J. ; Wang , Q. ; Zhu , J. ; Deng , J. Tetrahedron: Asymmetry 2012 , 23 , 457 – 460 .
   Web of Science ®Google Scholar
• (a) Jiang , B. ; Zhao , X.-L. ; Dong , J.-J. ; Wang , W.-J. Eur. J. Org. Chem. 2009 , 987 – 991 ; (b) Sun , J. ; Yang , M. ; Dai , Z. ; Zhu , C. ; Hu , H. Synthesis 2008 , 16 , 2513 – 2518 .
   Web of Science ®Google Scholar
• Choi , J. Y. ; Hwang , G.-S. ; Senapati , B. K. ; Ryu , D. H. Bull. Korean Chem. Soc. 2008 , 29 , 1879 – 1880 .
   Web of Science ®Google Scholar
• Dai , W. ; Li , J. ; Chen , B. ; Li , G. ; Lv , Y. ; Wang , L. ; Gao , S. Org. Lett. 2013 , 15 , 5658 – 5661 .
   PubMed Web of Science ®Google Scholar
• (a) Yoshida , T. ; Kito , M. ; Tsujii , M. ; Nagasawa , T. Biotechnol. Lett. 2001 , 23 , 1217 – 1222 ; (b) Babiak , P. ; Kysliková , E. ; Štěpánek , V. ; Valešová , R. ; Palyzová , A. ; Marešová , H. ; Hájíček , J. ; Kyslík , P. Bioresource Technol. 2011 , 102 , 7621 – 7626 .
   Web of Science ®Google Scholar
• Esomeprazole magnesium trihydrate. In European Pharmacopoeia 7.0; European Directorate for the Quality of Medicines HealthCare: Strasbourg, 2010; pp. 1951–1953 .
   Google Scholar
• (a) Korupoju , S. R. ; Zacharias , P. S. Chem. Commun. 1998 , 1267 – 1268 ; (b) Lin , S-Y. ; Guo , Y.-N. ; Guo , Y. ; Zhao , L. ; Zhang , P. ; Ke , H. ; Tang , J. Chem. Commun. 2012 , 6924 – 6926 ; (c) Paluch , M. ; Lisowski , J. ; Lis , T. Dalton Trans. 2006 , 381 – 388 ; (d) Kobylka , M. J. ; Janczak , J. ; Lis , T. ; Kowalik-Jankowska , T. ; Klak , J. ; Pietruszka , M. ; Lisowski , J. Dalton Trans. 2012 , 1053 – 1511 ; (e) Kobylka , M. J. ; Ślepokura , K. ; Rodicio , M. A. ; Paluch , M. ; Lisowski , J. Inorg. Chem. 2013 , 52 , 12893 – 12903 (f) Paluch , M. ; Ślepokura , K. ; Lis , T. ; Lisowski , J. Inorg. Chem. Commun. 2011 , 14 , 92 – 95 ; (g) Paluch , M. ; Lisowski , J. J. Alloys Compounds 2008 , 451 , 443 – 447 ; (h) Kuhnert , N. ; Rossignolo , G. M. ; Lopez-Periago , A. Org. Biomol. Chem. 2003 , 1 , 1157 – 1170 .
   Web of Science ®Google Scholar
• Korupoju , S. R. ; Mangayarkarasi , N. ; Zacharias , P. S. ; Mizuthani , J. ; Nishihara , H. Inorg. Chem. 2002 , 41 , 4099 – 4101 .
   PubMed Web of Science ®Google Scholar
• Gao , J. ; Zingaro , R. A. ; Reibenspies , J. H. ; Martell , A. E. Org. Lett. 2004 , 6 , 2453 – 2455 .
   PubMed Web of Science ®Google Scholar
• Tanaka , K. ; Fukuda , N. Tetrahedron: Asymmetry 2009 , 20 , 111 – 114 .
   Web of Science ®Google Scholar
• For introduction and recent reviews of SDE see (a) Soloshonok , V. A. Angew. Chem. Int. Ed. 2006 , 45 , 766 – 769 ; (b) Sorochinsky , A. E. ; Soloshonok , V. A. Self-disproportionation of enantiomers of enantiomerically enriched compounds. In Differentiation of Enantiomers II, Topics in Current Chemistry; V. Schurig, (Ed.); Springer-Verlag: Berlin, 2013; pp. 301–340 ; (c) Soloshonok , V. A. ; Roussel , C. ; Kitagawa , O. ; Sorochinsky , A. E. Chem. Soc. Rev. 2012 , 41 , 4180 – 4188 ; (d) Han , J. L. ; Nelson , D. J. ; Sorochinsky , A. E. ; Soloshonok , V. A. Curr. Org. Synth. 2011 , 8 , 310 – 317 ; (e) Martens , J. ; Bhushan , R. Helv. Chim. Acta 2014 , 97 , 161 – 187 ; (f) Faigl , F. ; Fogassy , E. ; Nógrádi , M. ; Pálovics , E. ; Schindler , J. Org. Biomol. Chem. 2010 , 8 , 947 – 959 ; (g) Sorochinsky , A. E. ; Acena , J. L. ; Soloshonok , V. A. Synthesis 2013 , 45 , 141 – 152 ; (h) Soloshonok , V. A. ; Berbasov , D. O. Chim. Oggi [Chem. Today] 2006 , 24 , 44 – 47 ; (i) Sorochinsky , A. E. ; Katagiri , T. ; Ono , T. ; Wzorek , A. ; Aceña , J. L. ; Soloshonok , V. A. Chirality 2013 , 25 , 365 – 368 . For SDE of chiral sulfoxides on achiral silica gel see (j) Diter , P. ; Taudien , S. ; Samuel , O. ; Kagan , H. B. J. Org. Chem. 1994 , 59 , 370 – 373 ; (k) Song , W. ; Zhou , Y. ; Fu , Y. ; Xu , W. Tetrahedron: Asymmetry 2013 , 24 , 909 – 912 ; (l) Wzorek , A. ; Klika , K. D. ; Drabowicz , J. ; Sato , A. ; Aceña , J. L. ; Soloshonok , V. A. Org. Biomol. Chem. 2014 , 12 , 4738 – 4746 .
   PubMed Web of Science ®Google Scholar
• The sodium salt of esomeprazole is easier to dry and more stable than potassium salt, but potassium salt is easier to be separated out from the reaction mixture .
   Google Scholar