Vanadium-catalyzed Enantioselective Sulfoxidation of Methyl Aryl Sulfides with Hydrogen Peroxide as Terminal Oxidant

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.

asymmetric catalysis - chiral vanadium complex - Schiff base - enantioselective sulfoxidation - hydrogen peroxide

References

<A NAME="RY22201ST-1A">1a</A> Kagan H. In Catalytic Asymmetric Synthesis   Ojima I. Wiley-VCH; New York: 2000.  Chap. 6c.

<A NAME="RY22201ST-1B">1b</A> Kagan H. In Asymmetric Oxidation Reactions: Practical Approach in Chemistry   Katsuki T. Oxford University Press; Oxford: 2001.  Chap. 4.1.

<A NAME="RY22201ST-2">2</A> Pitchen P. Dunach E. Deshmukh MN. Kagan HB. J. Am. Chem. Soc.  1984,  106:  8188 

<A NAME="RY22201ST-3">3</A> Di Furia F. Modena G. Seraglia R. Synthesis  1984,  325 

<A NAME="RY22201ST-4">4</A> Brunel JM. Kagan HB. Synlett  1996,  404 

For other catalytic asymmetric sulfoxidations, see:

<A NAME="RY22201ST-5A">5a</A> Yamamoto K. Ando H. Shuetake T. Chikamatsu H. J. Chem. Soc., Chem. Commun.  1989,  754 

<A NAME="RY22201ST-5B">5b</A> Komatsu N. Nishi-Bayashi Y. Sugita T. Uemura S. Tetrahedron Lett.  1992,  33:  5391 

<A NAME="RY22201ST-5C">5c</A> Boche G. Möbus K. Harms K. Marsch M. J. Am. Chem. Soc.  1996,  118:  2770 

<A NAME="RY22201ST-5D">5d</A> Liu G. Cogan DA. Ellman JA. J. Am. Chem. Soc.  1997,  119:  9913 

<A NAME="RY22201ST-5E">5e</A> Yamanoi Y. Imamoto T. J. Org. Chem.  1997,  62:  8560 

<A NAME="RY22201ST-5F">5f</A> Reetz MT. Merk C. Naberfeld G. Rudolph J. Griebenow N. Goddard R. Tetrahedron Lett.  1997,  38:  5273 

<A NAME="RY22201ST-5G">5g</A> Peng Y. Feng X. Cui X. Jiang Y. Chan ASC. Synth. Commun.  2001,  31:  2287 

<A NAME="RY22201ST-5H">5h</A> Skarzewski J. Ostrycharz E. Siedlecka R. Zielinska-Blajet M. Pisarski B. J. Chem. Res., Synop.  2001,  263 

<A NAME="RY22201ST-6A">6a</A> Nakajima K. Kojima M. Fujita J. Chem. Lett.  1986,  1483 

<A NAME="RY22201ST-6B">6b</A> Nakajima K. Kojima K. Kojima M. Fujita J. Bull. Chem. Soc. Jpn.  1990,  63:  2620 

<A NAME="RY22201ST-7">7</A> Palucki M. Hanson P. Jacobsen EN. Tetrahedron Lett.  1992,  33:  7111 

<A NAME="RY22201ST-8A">8a</A> Noda K. Hosoya N. Irie R. Yamashita Y. Katsuki T. Tetrahedron  1994,  50:  9609 

<A NAME="RY22201ST-8B">8b</A> Kokubo C. Katsuki T. Tetrahedron  1996,  52:  13895 

<A NAME="RY22201ST-9">9</A> Saito B. Katsuki T. Tetrahedron Lett.  2001,  42:  3873 

<A NAME="RY22201ST-10A">10a</A> Bolm C. Bienewald F. Angew. Chem., Int. Ed. Engl.  1995,  34:  2640 

<A NAME="RY22201ST-10B">10b</A> Bolm C. Bienewald F. Synlett  1998,  1327 

<A NAME="RY22201ST-11">11</A> Vetter AH. Berkessel A. Tetrahedron Lett.  1998,  39:  1741 

<A NAME="RY22201ST-12A">12a</A> Katsuki T. J. Mol. Cat. A: Chem.  1996,  113:  87 

<A NAME="RY22201ST-12B">12b</A> Ito YN. Katsuki T. Bull. Chem. Soc. Jpn.  1999,  72:  603 

<A NAME="RY22201ST-13">13</A>

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] ).

<A NAME="RY22201ST-14">14</A> Nishikori H. Katsuki T. Tetrahedron Lett.  1996,  37:  9245 

<A NAME="RY22201ST-15">15</A> Saito S. Kano T. Muto H. Nakadai M. Yamamoto H. J. Am. Chem. Soc.  1999,  121:  8943 

<A NAME="RY22201ST-16A">16a</A> Karpyshev NN. Yakovleva OD. Talsi EP. Bryliakov KP. Tolstikova OV. Tolstikov AG. J. Mol. Cat. A: Chem.  2000,  157:  91 

<A NAME="RY22201ST-16B">16b</A> Bryliakov KP. Karpyshev NN. Forminsky SA. Tolstikov AG. Talsi EP. J. Mol. Cat. A: Chem.  2001,  171:  73 

<A NAME="RY22201ST-17">17</A> Sakuraba H. Natori K. Tanaka Y. J. Org. Chem.  1991,  56:  4124