Synlett, Inhaltsverzeichnis LETTER © Georg Thieme Verlag Stuttgart · New York Vanadium-catalyzed Enantioselective Sulfoxidation of Methyl Aryl Sulfides with Hydrogen Peroxide as Terminal Oxidant Chisa Ohta, Hideki Shimizu, Akiko Kondo, Tsutomu Katsuki*Department of Chemistry, Faculty of Science, Graduate School, Kyushu University 33, Hakozaki, Higashi-ku, Fukuoka 812-8581, JapanFax: +81(92)6422607; e-Mail: katsuscc@mbox.nc.kyushu-u.ac.jp; Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract Chiral vanadium complex prepared in situ from VO(acac)2 and Schiff base 9 was found to be an efficient catalyst for oxidation of various methyl aryl sulfides with hydrogen peroxide as terminal oxidant. For example, oxidation of methyl 2-naphthyl sulfide using a VO(acac)2, 9, and hydrogen peroxide system proceeded with high enantioselectivity of 93% ee as well as acceptable chemical yield. Key words asymmetric catalysis - chiral vanadium complex - Schiff base - enantioselective sulfoxidation - hydrogen peroxide Volltext Referenzen References 1a Kagan H. In Catalytic Asymmetric Synthesis Ojima I. Wiley-VCH; New York: 2000. Chap. 6c. 1b Kagan H. In Asymmetric Oxidation Reactions: Practical Approach in Chemistry Katsuki T. Oxford University Press; Oxford: 2001. Chap. 4.1. 2 Pitchen P. Dunach E. Deshmukh MN. Kagan HB. J. Am. Chem. Soc. 1984, 106: 8188 3 Di Furia F. Modena G. Seraglia R. Synthesis 1984, 325 4 Brunel JM. Kagan HB. Synlett 1996, 404 For other catalytic asymmetric sulfoxidations, see: 5a Yamamoto K. Ando H. Shuetake T. Chikamatsu H. J. Chem. Soc., Chem. Commun. 1989, 754 5b Komatsu N. Nishi-Bayashi Y. Sugita T. Uemura S. Tetrahedron Lett. 1992, 33: 5391 5c Boche G. Möbus K. Harms K. Marsch M. J. Am. Chem. Soc. 1996, 118: 2770 5d Liu G. Cogan DA. Ellman JA. J. Am. Chem. Soc. 1997, 119: 9913 5e Yamanoi Y. Imamoto T. J. Org. Chem. 1997, 62: 8560 5f Reetz MT. Merk C. Naberfeld G. Rudolph J. Griebenow N. Goddard R. Tetrahedron Lett. 1997, 38: 5273 5g Peng Y. Feng X. Cui X. Jiang Y. Chan ASC. Synth. Commun. 2001, 31: 2287 5h Skarzewski J. Ostrycharz E. Siedlecka R. Zielinska-Blajet M. Pisarski B. J. Chem. Res., Synop. 2001, 263 6a Nakajima K. Kojima M. Fujita J. Chem. Lett. 1986, 1483 6b Nakajima K. Kojima K. Kojima M. Fujita J. Bull. Chem. Soc. Jpn. 1990, 63: 2620 7 Palucki M. Hanson P. Jacobsen EN. Tetrahedron Lett. 1992, 33: 7111 8a Noda K. Hosoya N. Irie R. Yamashita Y. Katsuki T. Tetrahedron 1994, 50: 9609 8b Kokubo C. Katsuki T. Tetrahedron 1996, 52: 13895 9 Saito B. Katsuki T. Tetrahedron Lett. 2001, 42: 3873 10a Bolm C. Bienewald F. Angew. Chem., Int. Ed. Engl. 1995, 34: 2640 10b Bolm C. Bienewald F. Synlett 1998, 1327 11 Vetter AH. Berkessel A. Tetrahedron Lett. 1998, 39: 1741 12a Katsuki T. J. Mol. Cat. A: Chem. 1996, 113: 87 12b Ito YN. Katsuki T. Bull. Chem. Soc. Jpn. 1999, 72: 603 13 Although we synthesized compound 8 according to the reported procedure (ref. [14] ), it can be prepared enantioselectively in a short step by using Yamamoto procedure (ref. [15] ). 14 Nishikori H. Katsuki T. Tetrahedron Lett. 1996, 37: 9245 15 Saito S. Kano T. Muto H. Nakadai M. Yamamoto H. J. Am. Chem. Soc. 1999, 121: 8943 16a Karpyshev NN. Yakovleva OD. Talsi EP. Bryliakov KP. Tolstikova OV. Tolstikov AG. J. Mol. Cat. A: Chem. 2000, 157: 91 16b Bryliakov KP. Karpyshev NN. Forminsky SA. Tolstikov AG. Talsi EP. J. Mol. Cat. A: Chem. 2001, 171: 73 17 Sakuraba H. Natori K. Tanaka Y. J. Org. Chem. 1991, 56: 4124
