A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans.
A new mode of cyclobutenedione ring opening for the synthesis of 2-oxobut-3-enamides and tetrasubstituted furans.
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DOI：
10.1039/d1cc02097h
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发表时间：
2021-05
影响因子：
4.9
通讯作者：
Ryan M Bennett;Wei Sun;Dharyl C Wilson;M. Light;D. Harrowven
中科院分区：
文献类型：
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作者：
Ryan M Bennett;Wei Sun;Dharyl C Wilson;M. Light;D. Harrowven
描述了有机锂和氨基锂加成到环丁烯二酮上的二分法，其中前者得到羰基加成产物，而后者通过O-到C-锂转移通过烯酮裂解诱导开环。这种独特的断环模式可以获得2-氧代丁-3-烯酰胺和四取代呋喃。
A dichotomy between the additions of organolithiums and lithium amides to cyclobutenediones is described wherein the former give carbonyl addition products while the latter induce ring opening by enone cleavage via O- to C-lithium transfer. This distinct mode of ring scission gives access to 2-oxobut-3-enamides and tetrasubstituted furans.