菲烷类化合物的合成研究。钯催化的分子内烯丙基化反应高非对映选择性构建 4,5-螺环。
Synthetic Study of Phainanoids. Highly Diastereoselective Construction of the 4,5-Spirocycle via Palladium-Catalyzed Intramolecular Alkenylation.
机构信息
Department of Chemistry, University of Chicago , 5735 South Ellis Avenue, Chicago, Illinois 60637, United States.
出版信息
Org Lett. 2017 Jun 2;19(11):3017-3020. doi: 10.1021/acs.orglett.7b01303. Epub 2017 May 19.
An efficient strategy to synthesize the western part of phainanoids is reported. The benzofuranone-based 4,5-spirocyclic motif is constructed diastereoselectively via a palladium-catalyzed intramolecular alkenylation. The computational study suggests that the remarkably high diastereoselectivity is attributed to the stabilizing interaction between the 2' carbonyl moiety and the palladium catalyst in the favored transition state.
报道了一种高效合成菲烷类化合物西部结构的策略。通过钯催化的分子内烯丙基化反应，立体选择性地构建了基于苯并呋喃酮的 4,5-螺环骨架。计算研究表明，在有利的过渡态中，2' 羰基部分与钯催化剂之间的稳定相互作用导致了显著的高立体选择性。
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