Issue 2, 2018

Gold(i) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)

Abstract

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 Caryl-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.

Graphical abstract: Gold(i) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)

Supplementary files

Article information

Article type
Research Article
Submitted
15 Aug 2017
Accepted
27 Sep 2017
First published
28 Sep 2017

Org. Chem. Front., 2018,5, 197-202

Gold(I) catalyzed cascade cyclization: intramolecular two-fold nucleophilic addition to vinylidenecyclopropanes (VDCPs)

W. Zang, Y. Wei and M. Shi, Org. Chem. Front., 2018, 5, 197 DOI: 10.1039/C7QO00722A

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