The Asymmetric Oxidation of Sulfides Catalyzed by Chiral Oxazoline-Ti(Ⅳ) Complexes

Chem. J. Chinese Universities ›› 2001, Vol. 22 ›› Issue (8): 1326.

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The Asymmetric Oxidation of Sulfides Catalyzed by Chiral Oxazoline-Ti(Ⅳ) Complexes

PENG Yun-Gui², FENG Xiao-Ming^1,2, CUI Xin², JIANG Yao-Zhong²

1. The Faculty of Chemistry, Sichuan University, Chengdu 610064, China;
2. Union Laboratory of Asymmetric Synthesis, Chengdu Instituteof Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China

Received:2000-09-30 Online:2001-08-24 Published:2001-08-24

Abstract

Abstract: Aseries of new chiral oxazoline-Ti(OⁱPr)₄ complexes were synthesized, which were firstly and successfully applied to the catalytic asymmetric oxidation of sulfides and resulteDIn chiral sulfoxides. The reactivity and enantioselectivity were strongly influenced by the structure of the oxazolines. When (4S,5S )-4,5-dihydro-4,5-diphenyl-2-(2'-hydroxy-3'-tert-butylphenyl) oxazoline was used as the ligand, 2.0 mol of TBHPwas useDIn the oxidation of methyl phenyl sulfide, the sulfoxide was obtaineDIn₉₆% e.e. . The influence of solvent, amount of catalyst, counterion and other conditions on the reaction was also investigated.

Key words: Oxazoline Ti(O-i-Pr)₄ complex, Catalysis, Sulfide, Asymmetric oxidation

CLC Number:

O621
O251

TrendMD:

PENG Yun-Gui, FENG Xiao-Ming, CUI Xin, JIANG Yao-Zhong . The Asymmetric Oxidation of Sulfides Catalyzed by Chiral Oxazoline-Ti(Ⅳ) Complexes[J]. Chem. J. Chinese Universities, 2001, 22(8): 1326.

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The Asymmetric Oxidation of Sulfides Catalyzed by Chiral Oxazoline-Ti(Ⅳ) Complexes

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