Diastereoselective synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones
Diastereoselective synthesis of 3,6-disubstituted 3,6-dihydropyridin-2-ones
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DOI：
10.1016/s0040-4039(02)02677-1
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发表时间：
2003-01-20
影响因子：
1.8
通讯作者：
Tchabanenko, K
中科院分区：
文献类型：
--
作者：
Anderson, TF;Knight, JG;Tchabanenko, K
在一个短的序列中，5-乙烯基恶唑烷-2-酮通过Pd催化的羰基化和烯醇化物烷基化以高的非对映选择性转化为3，6-二取代的3，6-二氢吡啶-2-酮。6-取代的N-甲基吡啶-2-酮与MeI、BuI和i-PrI的烷基化反应立体选择性地生成3，6-反式非对映异构体。相应的N-BOC吡啶酮的烷基化反应高选择性地得到3，6-顺式非对映异构体。(C)2003爱思唯尔科技有限公司版权所有。
In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihydropyridin-2-ones via Pd-catalysed carbonylation and enolate alkylation with high diastereoselectivity. Alkylation of 6-substituted N-methylpyridin-2-ones gives stereoselectively the 3,6-anti diastereoisomer with MeI, BuI and i-PrI. Alkylation of the corresponding N-BOC pyridinones gives the 3,6-syn diastereoisomer with high selectivity. (C) 2003 Elsevier Science Ltd. All rights reserved.