Asymmetric radical reaction in the coordination sphere. IV. Ruthenium(II)-catalyzed asymmetric addition of sulfonyl chloride to 1-phenylpropene.
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概要
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The asymmetric addition of methane- and <I>p</I>-toluenesulfonyl chloride to 1-phenylpropene catalyzed by Ru<SUB>2</SUB>Cl<SUB>4</SUB>[(−)-diop]<SUB>3</SUB> affords optically active 1:1 adducts, (+)-(1<I>R</I>,2<I>RS</I>)-1-chloro-2-methylsulfonyl-1-phenylpropane (<B>2</B>) and (+)-(1<I>R</I>,2<I>RS</I>)-1-chloro-1-phenyl-2-tosylpropane (<B>3</B>), with about 13–19%ee. Similarly, (−)-(1<I>S</I>,2<I>RS</I>)-<B>2</B> and (−)-(1<I>S</I>,2<I>RS</I>)-<B>3</B> were obtained when Ru<SUB>2</SUB>Cl<SUB>4</SUB>[(+)-diop]<SUB>3</SUB> was employed. A enantiolace differentiation is considered to occur in the chlorine atom transferring step from the ruthenium(III) species to the carbon radical in the coordination sphere.
- 公益社団法人 日本化学会の論文
著者
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Kamigata Nobumasa
Department Of Chemistry Faculty Of Science Tokyo Metropolitan University
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Kameyama Masayuki
Department of Chemistry, Faculty of Science, Tokyo Metropolitan University
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- Asymmetric radical reaction in the coordination sphere. IV. Ruthenium(II)-catalyzed asymmetric addition of sulfonyl chloride to 1-phenylpropene.