在三氟甲磺酸三甲基硅酯介导的炔基烯醇碳酸酯反应中，丙烯酸酯部分的转位生成杂环二烯。
Transposition of an acrylate moiety in TMSOTf-mediated reaction of alkynyl vinylogous carbonates gives heterocyclic dienes.
作者信息
Gharpure Santosh J, Fartade Dipak J, Gupta Krishna S, Patel Raj K
机构信息
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai - 400076, India.
出版信息
Chem Commun (Camb). 2022 Aug 30;58(70):9762-9765. doi: 10.1039/d2cc03802a.
TMSOTf-mediated reaction of alkynyl vinylogous carbonates serendipitously gave 1,4-oxazepine and dihydropyran dienes transposition of an ethyl acrylate moiety involving intramolecular cascade Prins-type cyclization/retro-oxa-Michael reaction/cycloisomerisation. The developed atom-economical protocol selectively provides an double bond geometry. Dihydropyran dienes could be reduced diastereoselectively using EtSiH/TMSOTf or could be transformed into polycyclic heterocycles by Heck reaction.
三氟甲磺酸三甲基硅酯介导的炔基烯醇碳酸酯反应意外地生成了1,4-恶唑并庚因和二氢吡喃二烯，其中丙烯酸乙酯部分发生了分子内级联普林斯型环化/逆氧杂迈克尔反应/环异构化的双键迁移。所开发的原子经济协议选择性地提供了一种双键几何结构。二氢吡喃二烯可以使用EtSiH/三氟甲磺酸三甲基硅酯进行非对映选择性还原，或者通过赫克反应转化为多环杂环化合物。
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