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通过 N-杂环卡宾/路易斯酸协同催化改变 2-糠醛基肉桂酸二聚反应途径：碳-碳键的异常断裂。

Changing reaction pathways of the dimerization of 2-formylcinnamates by N-heterocyclic carbene/Lewis acid cooperative catalysis: an unusual cleavage of the carbon-carbon bond.

机构信息

College of Chemistry, Beijing Normal University , Beijing 100875, China.

出版信息

Org Lett. 2014 Nov 7;16(21):5520-3. doi: 10.1021/ol502791s. Epub 2014 Oct 20.

DOI:10.1021/ol502791s
PMID:25329247
Abstract

Catalyzed by a triazole carbene, the dimerization of 2-formylcinnamates underwent benzoin condensation followed by intramolecular oxa-Michael addition to afford isochromeno[4,3-c]isochromene products. Under the catalysis of a combination of triazole carbene and Ti(OPr-i)4 catalysts, the dimerization reaction of 2-formylcinnamates proceeded through a completely different route to furnish the formation of isochromenone derivatives with the elimination of an acetate moiety.

摘要

三氮唑卡宾催化 2-醛基肉桂酸酯二聚，经历安息香缩合，随后发生分子内氧杂-Michael 加成，生成异色满并[4,3-c]异色满产物。在三氮唑卡宾和 Ti(OPr-i)4 催化剂的共同催化下，2-醛基肉桂酸酯的二聚反应通过完全不同的途径进行，以消除醋酸酯部分的方式生成异色酮衍生物。

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