Asymmetric oxidation of 1,3-dithianes to 1,3-dithiane 1-oxides
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概要
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Oxidation of 2-(1-hydroxy-1-methylethyl)-1,3-dithiane with the Sharpless reagent has been examined under various reaction conditions. Oxidation of 2-(1-hydroxy-1-methylethyl)-1,3-dithiane with Ti(OPri)4-diethyl L-(+)-tartrate-tert-butyl hydroperoxide (1:2:1.5) in CH2Cl2 in the presence of 4 A molecular sieves gives (1S,2S)-2-(1-hydroxy-1-methylethyl)-1,3-dithiane 1-oxide with high trans selectivity and with moderate enantioselectivity. The enantioselectivity depends upon the substituent at the 2-position of the 1,3-dithiane. Oxidation of 2-(1-methoxy-1-methylethyl)- and 2-(1-acetoxy-1-methylethyl)-1,3-dithiane gives (1S,2S)-2-(1-methoxy-1-methylethyl)- and (1R,2S)-2-(1-acetoxy-1-methylethyl)-1,3-dithiane 1-oxides, respectively in >99% ee.
- Royal Society of Chemistryの論文
- 1998-01-01
Royal Society of Chemistry | 論文
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