Base-induced cyclization of N-(bis(ethoxycarbonyl)methyl)-2-bromo-3-hydroxybutyramide derivatives.
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概要
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Treatment of (2<I>R</I>,3<I>R</I>)-<I>N</I>-(2,4-dimethoxybenzyl)-<I>N</I>-[bis(ethoxycarbonyl)methyl]-2-bromo-3-hydroxybutyramide (<B>5</B>) with DBU yielded the bicyclic β-actam <B>13</B> by a direct cyclization, and its diastereoisomer <B>14</B> and the γ-lactam <B>15</B> <I>via</I> the <I>trans</I>-epoxide <B>6</B>. The same treatment of (2<I>S</I>,3<I>R</I>)-isomer (<B>11</B>) gave the direct cyclization product <B>14</B> in 93% yield. On the other hand, reaction of <B>5</B> and <B>11</B> with sodium hydride afforded the 2-azetidinone derivatives (mainly <B>14</B> (23%) from <B>5</B>, and <B>19</B> (75%) from <B>11</B>, respectively) <I>via</I> the corresponding epoxides <B>6</B> and <B>12</B>.
- 公益社団法人 日本化学会の論文
著者
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Hiraoka Tetsuo
Chemical Research Laboratories of Sankyo Company Limited
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Ishida Noboru
Chemical Research Laboratories of Sankyo Company Limited
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Shiozaki Masao
Chemical Research Laboratories of Sankyo Company Limited
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Maruyama Hiroshi
Chemical Research Laboratories of Sankyo Company Limited
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- A synthesis of optically active 4-diethoxyphosphinyl-3-(1-hydroxyethyl)-2-azetidinone : A potential precursor to (1-aminoalkyl)-phosphonic acid derivatives.
- Base-induced cyclization of N-(bis(ethoxycarbonyl)methyl)-2-bromo-3-hydroxybutyramide derivatives.