Gold(i) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)†,Organic Chemistry Frontiers

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Gold(i) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2017-09-28 00:00:00 , DOI: 10.1039/c7qo00722a
Wenqing Zang _{1,

2,

3,

4,

5} , Yin Wei _{1,

2,

3,

4,

5} , Min Shi _{1,

2,

3,

4,

5}

Affiliation

A gold-catalyzed cascade cyclization of vinylidenecyclopropanes (VDCPs) bearing a naphthyl moiety and an ortho-alkoxylmethyl group has been reported in this paper, affording spiro[cyclopenta[a]naphthalene-1,1′-cyclopropanes] in moderate to good yields. The reaction proceeded through a two-fold intramolecular nucleophilic addition (O-nucleophilic addition and then C_aryl-nucleophilic addition) to a vinylidenecyclopropane moiety to give a highly strained intermediate and subsequent retro-Diels–Alder addition. The reaction mechanism has been investigated on the basis of a deuterium labeling experiment, mass spectrometric investigation and DFT calculation.

中文翻译：

金（i）催化的级联环化：分子内的两倍亲核加成到亚乙烯基亚环丙烷（VDCPs）中†

本文报道了金催化的带有萘基部分和邻烷氧基甲基的亚乙烯基亚环丙烷（VDCPs）的级联环化反应，提供了中等至良好收率的螺环[环戊[ a ]萘-1,1'-环丙烷]。该反应通过向亚乙烯基环丙烷部分进行两次分子内亲核加成（O-亲核加成，然后C_芳基-亲核加成）进行，从而得到高度紧张的中间体，随后进行逆Diels-Alder加成。在氘标记实验，质谱研究和DFT计算的基础上，研究了反应机理。

更新日期：2017-09-28

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