The preparation of optically active .BETA.-keto sulfoxides by means of an enantiomer-differentiating reaction of .ALPHA.-lithio aryl methyl sulfoxides with chiral carboxylates.
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概要
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The reaction of α-lithio aryl methyl sulfoxides with a limited amount of chiral carboxylates (R<SUP>2</SUP>–CO–O–R<SUP>*</SUP>) was found to be an enantiomer-differentiating reaction, affording the corresponding optically active β-keto sulfoxides (<B>3</B>), together with optically active aryl methyl sulfoxides which have the opposite configuration. The optical purity and the predominant configuration of <B>3</B> obtained were assigned by means of a combination of polarimetric analysis and NMR. The degree of enantioselectivity of this reaction was affected by the nature of the ester moiety R<SUP>2</SUP>, indicating an increase in optical yields, from 1.3%, where R<SUP>2</SUP> was ethyl (<B>3b</B>), to 70.3%, where R<SUP>2</SUP> was <I>t</I>-butyl (<B>3f</B>). The stereochemical course of the reaction has been discussed by considering a six-membered cyclic transition state. Furthermore, the repeated recrystallizations of several β-keto sulfoxides thus obtained, such as (−)-<B>3e</B>, (−)-<B>3f</B>, (−)-<B>3g</B>, and (−)-<B>3p</B>, were found to give the corresponding highly optically pure β-keto sulfoxides.
- 公益社団法人 日本化学会の論文
著者
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Kinoshita Masayoshi
Department Of Bioapplied Chemistry Faculty Of Engineering Osaka City University
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Kunieda Norio
Department Of Applied Chemistry Faculty Of Engineering Osaka City University
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Suzuki Akira
Department Of Anesthesiology And Intensive Care Hamamatsu University School Of Medicine
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Suzuki Akira
Department of Applied Chemistry, Faculty of Engineering, Osaka City University
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Kinoshita Masayoshi
Department of Applied Chemistry, Faculty of Engineering, Osaka City University
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