Asymmetric Synthesis with Sugar Derivatives. V. The Synthesis of α-Hydroxy Acids on Insoluble Polymer Supports
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概要
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The styrene-2% divinylbenzene copolymer containing 1,2-<I>O</I>-cyclohexylidene-5-<I>O</I>-trityl-α-D- or -L-xylofuranose (D- or L-<B>3a</B>) was prepared. Asymmetric Grignard additions to benzoylformate (<B>3b</B>) and pyruvate (<B>3c</B>) were carried out using these polymers as chiral ester-components. Enantiomers of α-hydroxy acids, such as atrolactic acid (<B>4</B>) and 2-hydroxy-2-phenyl-2-(<I>p</I>-tolyl)acetic acid (<B>5</B>), were obtained in relatively good synthetic and optical yields, depending on the use of either D- or L-<B>3a</B>. The optical yields of <B>4</B> for the polymer were higher than those for a low-molecular-weight compound, 1,2-<I>O</I>-cyclohexylidene-5-<I>O</I>-trityl-α-D-xylofuranose (<B>8a</B>). It was shown that the polymer could be used repeatedly.
- 公益社団法人 日本化学会の論文
著者
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Emoto Sakae
The Institute of Physical and Chemical Research
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Kawana Masajiro
The Institute of Physical and Chemical Research
関連論文
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