UTILIZATION OF MOLYBDENUM-ALLYL COMPOUNDS FOR SYNTHESIS OF ALPHA -METHYLENEBUTYROLACTONES
UTILIZATION OF MOLYBDENUM-ALLYL COMPOUNDS FOR SYNTHESIS OF ALPHA -METHYLENEBUTYROLACTONES
复制标题
利用烯丙基钼化合物合成α-亚甲基丁内酯
DOI：
10.1021/om00004a015
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发表时间：
1995
期刊：
影响因子：
2.8
通讯作者：
Rai‐Shung Liu
中科院分区：
文献类型：
--
作者：
Shie;Chi;W. Vong;Rai‐Shung Liu
- 亚甲基丁内酯是许多天然化合物的重要结构单元，其活性在生物代谢中的重要性已被公认。过渡金属催化合成-亚甲基丁内酯的反应在催化和化学计量两方面都有很好的发展。在前者中，钯催化的环羰基化高炔丙醇2是特别有吸引力的，因为容易获得的起始原料和温和的操作条件。化学计量学上，α-甲基丁内酯的最方便的一步合成包括醛与2-（烷氧羰基）烯丙基锌、13 - 3镍、4-铬、5锡6和硅烷7的反应，如方案1所示。虽然上述反应中的一些以高非对映选择性进行，但它们中的一些处理了非对映选择性。
-Methylenebutyrolactone is an important structural unit1 in many naturally occurring compounds, and the importance of its activity inbiological metabolism is well recognized. Transition-metal-mediated synthesis of-methylenebutyrolactone from common organic chemi-cals is well developed in both catalytic and stoichiomet-ric reactions. In the former, the palladium-catalyzed cyclocarbonylation of homopropargyl alcohol2 is particu-larly attractive because of the easily accessible starting material and mild operating conditions. Stoichiomet-rically, themost convenient one-step synthesis of a-me-thylenebutyrolactone involves reactions of aldehydes with 2-(alkoxycarbonyl) allylic zinc, 13’3 nickel, 4-chromium, 5 tin6 and silanes7 as depicted in Scheme 1. Although some of the reactions above proceed with high diastereoselectivities, fewlc of them deal with the ste-