Asymmetric Construction of Spirocyclopentenebenzofuranone Core Structures via Highly Selective Phosphine-Catalyzed [3+2] Cycloaddition Reactions
Asymmetric Construction of Spirocyclopentenebenzofuranone Core Structures via Highly Selective Phosphine-Catalyzed [3+2] Cycloaddition Reactions
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DOI：
10.1021/ol401087a
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发表时间：
2013-06-21
期刊：
影响因子：
5.2
通讯作者：
Barbas, Carlos F., III
中科院分区：
文献类型：
--
作者：
Albertshofer, Klaus;Tan, Bin;Barbas, Carlos F., III
报道了3-取代亚甲基苯并呋喃酮衍生物与Morita-Baylis-Hillman碳酸酯的有机催化不对称[3 + 2]环加成反应，一步合成了多取代螺环戊烯苯并呋喃酮骨架。C2-对称磷杂环戊烷在温和条件下是该转化的有效亲核催化剂，提供由三个连续的立体中心组成的反应产物，包括一个全碳中心，具有优异的对映选择性。
An efficient organocatalytic asymmetric [3 + 2] cycloaddition reaction between 3-substituted methylenebenzofuranone derivatives and diverse Morita-Baylis-Hillman carbonates to provide complex polysubstituted spirocyclopentenebenzofuranone scaffolds In a single step is reported. C2-symmetric phospholanes were efficient nucleophilic catalysts of this transformation under mild conditions, providing reaction products comprised of three consecutive stereocenters, including one all-carbon center, with excellent enantioselectivity.