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炔烃对 Rautenstrauch 中间体的捕获用于 [5+2] 环加成：铑催化的 3-酰氧基-4-烯-1,9-二炔的环异构化反应生成双环[5.3.0]癸三烯。

Interception of a Rautenstrauch intermediate by alkynes for [5+2] cycloaddition: rhodium-catalyzed cycloisomerization of 3-acyloxy-4-ene-1,9-diynes to bicyclo[5.3.0]decatrienes.

机构信息

The School of Pharmacy, University of Wisconsin, Madison, 53705-2222, USA.

出版信息

Angew Chem Int Ed Engl. 2011 Aug 22;50(35):8153-6. doi: 10.1002/anie.201103136. Epub 2011 Jul 11.

DOI:10.1002/anie.201103136
PMID:21748834
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3399041/
Abstract

Rholling in the bicycles: a rhodium(I)-catalyzed cycloisomerization for the synthesis of bicyclic compounds containing a cycloheptatriene ring from linear alkenynes (see scheme; cod=1,5-cyclooctadiene) is proposed to proceed through 1,2-acyloxy migration, 6 π electrocyclization, migratory insertion, and reductive elimination. The overall process can be viewed as a novel intramolecular [5+2] cycloaddition with concomitant 1,2-acyloxy migration.

摘要

螺环化反应

铑（I）催化的环异构化反应用于合成含有环庚三烯环的双环化合物，该反应由线性炔烃（见方案；cod=1,5-环辛二烯）引发，经过 1,2-酰氧基迁移、6π电环化、迁移插入和还原消除等步骤。整个过程可以看作是一种新型的分子内[5+2]环加成反应，同时伴有 1,2-酰氧基迁移。

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An atom-economic synthesis of bicyclo[3.1.0]hexanes by rhodium N-heterocyclic carbene-catalyzed diastereoselective tandem hetero-[5+2] cycloaddition/Claisen rearrangement reaction of vinylic oxiranes with alkynes.通过铑氮杂环卡宾催化的立体选择性串联杂[5+2]环加成/乙烯基环氧化物与炔烃的Claisen 重排反应，原子经济性合成双环[3.1.0]己烷。
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