Phosphine-Initiated Cascade Annulation of beta '-Acetoxy Allenoate and p-Quinols: Access to Ring Fused Hexahydroindeno Furan Derivatives
Phosphine-Initiated Cascade Annulation of beta '-Acetoxy Allenoate and p-Quinols: Access to Ring Fused Hexahydroindeno Furan Derivatives
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DOI：
10.1002/adsc.201800319
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发表时间：
2018
影响因子：
5.4
通讯作者：
Shi Min
中科院分区：
文献类型：
--
作者：
Xing Jiao-Jiao;Gao Yu-Ning;Shi Min
以β′-乙酰氧基丙二烯酸酯为原料，膦催化对苯醌与β′-乙酰氧基丙二烯酸酯的高非对映选择性级联成环反应，一步生成三个连续的立体异构碳中心，得到高官能化的多环稠合六氢茚并呋喃衍生物。这种膦催化环化反应的突出特点包括在级联反应中使用对苯二酚的三个活性位点，底物范围广，优异的官能团耐受性，温和的反应条件，不对称形式，良好的产率，易于放大到克规模，以及进一步的转化。
A highly diastereoselective cascade annulation process ofp‐quinols with β′‐acetoxy allenoate catalyzed by phosphine has been developed, which comes up with highly functionalized multiple ring‐fused hexahydroindeno furan derivatives in synthetically useful yields and creates three consecutive stereogenic carbon centers only in a one‐step manner. The salient features of this phosphine‐catalyzed cyclization include the use ofp‐quinol's three active sites in this cascade reaction, wide substrate scope, excellent functional group tolerance, mild reaction conditions, asymmetric version, good yields, ease of scale‐up to gram scale, and further transformations.