Hypervalent Iodine(V)-Induced Asymmetric Oxidation of Sulfides to Sulfoxides Mediated by Reversed Micelles:  Novel Nonmetallic Catalytic System

Although several types of chiral hypervalent iodine reagents have been used for asymmetric induction, all of them have needed more than a stoichiometric amount of chiral reagents and have shown low enantioselectivities. The described new catalytic asymmetric oxidation using a hypervalent iodine(V) r...

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Bibliographic Details
Published in:Journal of organic chemistry 1999-05, Vol.64 (10), p.3519-3523
Main Authors: Tohma, Hirofumi, Takizawa, Shinobu, Watanabe, Hiroaki, Fukuoka, Yuko, Maegawa, Tomohiro, Kita, Yasuyuki
Format: Article
Language:English
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Summary:Although several types of chiral hypervalent iodine reagents have been used for asymmetric induction, all of them have needed more than a stoichiometric amount of chiral reagents and have shown low enantioselectivities. The described new catalytic asymmetric oxidation using a hypervalent iodine(V) reagent, iodoxybenzene (PhIO2), in a cationic reversed micellar system provides the first example of a catalytic asymmetric oxidation of sulfides to sulfoxides in high chemical yield with moderate to good enantioselectivity without the use of any transition-metal catalysts. The solubilization and activation of PhIO2 by adding catalytic amounts of both cetyltrimethylammonium bromide (CTAB) and a chiral tartaric acid derivative were found to be indispensable for the enhancement of chemical and optical yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo982295t