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Synfacts 2005(2): 0217-0217  
DOI: 10.1055/s-2005-916084
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Titanium(IV)-Catalyzed Enantioselective Sulfenylation of β-ketoesters

Contributor(s): Mark Lautens, Josephine Yuen
M. Jereb, A. Togni*
ETH Hönggerberg, zürich, Switzerland
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Publikationsdatum:
25. Oktober 2005 (online)

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Significance

The enantioselective sulfenylation of β-ketoesters using a [Ti(TADDOLato)] complex and phenylsulfenyl chloride is described. The catalyst is compatible with acidic conditions since it is unnecessary to add any base to neutralize the HCl formed during the reaction. This is advantageous compared to alternative methods. Enantio­selectivities were enhanced with the use of bulkier ester groups, with the t-butyl group giving the highest ee of 88%.