路易斯酸催化三重态敏化的苯乙烯烯烃的对映选择性交叉光环加成反应。
Enantioselective Crossed Photocycloadditions of Styrenic Olefins by Lewis Acid Catalyzed Triplet Sensitization.
机构信息
Department of Chemistry, University of Wisconsin-Madison, 1101 University Avenue, Madison, WI, 53726, USA.
出版信息
Angew Chem Int Ed Engl. 2017 Sep 18;56(39):11891-11895. doi: 10.1002/anie.201706975. Epub 2017 Aug 30.
Abstract
The synthesis of unsymmetrical cyclobutanes by controlled heterodimerization of olefins remains a substantial challenge, particularly in an enantiocontrolled fashion. Shown herein is that chiral Lewis acid catalyzed triplet sensitization enables the synthesis of highly enantioenriched diarylcyclobutanes by photocycloaddition of structurally varied 2'-hydroxychalcones with a range of styrene coupling partners. The utility of this reaction is demonstrated through the direct synthesis of a representative norlignan cyclobutane natural product.
摘要
通过控制烯烃的杂二聚反应来合成非对称环丁烷仍然是一个巨大的挑战，特别是在对映选择性控制方面。本文展示了手性路易斯酸催化三重态敏化作用能够通过结构多样的 2'-羟基查耳酮与一系列苯乙烯偶联试剂的光环加成反应来合成高度对映富集的二芳基环丁烷。该反应的实用性通过直接合成具有代表性的愈创木烷环丁烷天然产物得到了证明。
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