Novel synthesis of pyrrolidinones by cobalt carbonyl catalyzed carbonylation of azetidines. A new ring-expansion-carbonylation reaction of 2-vinylazetidines to tetrahydroazepinones
Novel synthesis of pyrrolidinones by cobalt carbonyl catalyzed carbonylation of azetidines. A new ring-expansion-carbonylation reaction of 2-vinylazetidines to tetrahydroazepinones
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DOI：
10.1021/ja00201a040
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发表时间：
1989-09
影响因子：
15
通讯作者：
D. Roberto;H. Alper
中科院分区：
文献类型：
--
作者：
D. Roberto;H. Alper
氮杂环己烷在钴催化下的羰基化反应可以高产率、高区域选择性地合成吡咯烷酮类化合物。对于2-取代氮杂环丁烷(烷基、芳基、CH2OH、CH2OR、CH2OCOR和CoOR)，根据取代基的种类和反应温度，在或多或少取代环的碳-氮键上发生羰基插入。在2-乙烯基氮杂环丁烷的情况下，扩环和烷基化得到七元环四氢氮杂环酮。在这些反应中观察到了良好的官能团耐受性
Pyrrolidinones can be synthesized in high yields and regioselectivity by the cobalt carbonyl catalyzed carbonylation of azetidines. For 2-substituted azetidines (alkyl, aryl, CH 2 OH, CH 2 OR, CH 2 OCOR, and COOR), carbonyl insertion occurs in the more or less substituted ring carbon-nitrogen bond depending on the kind of substituent group and on the reaction temperature. In the case of 2-vinylazetidines, ring expansion and crbonylation affords seven-membered-ring tetrahydroazepinones. Good functional group tolerance was observed in these reactions