An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor–acceptor cyclopropanes with malononitrile

Manas K. Ghorai; Ranadeep Talukdar; Deo Prakash Tiwari

doi:10.1039/C3CC44533J

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An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor–acceptor cyclopropanes with malononitrile†

Manas K. Ghorai,*^a Ranadeep Talukdar^a and Deo Prakash Tiwari^a

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* Corresponding authors

^a Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India
E-mail: mkghorai@iitk.ac.in
Fax: +91-512-2597436
Tel: +91-512-2597518

Abstract

A highly efficient strategy for the synthesis of functionalised carbocyclic enaminonitriles in excellent yields has been described. The reaction utilises Yb(OTf)₃ catalysed C–C bond cleavage and two simultaneous C–C bond formations of donor–acceptor (DA)-cyclopropanes with malononitrile anions in a domino fashion.

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DOI: https://doi.org/10.1039/C3CC44533J
Article type: Communication
Submitted: 17 Jun 2013
Accepted: 17 Jul 2013
First published: 18 Jul 2013

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Chem. Commun., 2013,49, 8205-8207

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An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor–acceptor cyclopropanes with malononitrile

M. K. Ghorai, R. Talukdar and D. P. Tiwari, Chem. Commun., 2013, 49, 8205 DOI: 10.1039/C3CC44533J

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Chemical Communications

An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor–acceptor cyclopropanes with malononitrile†

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An efficient synthetic route to carbocyclic enaminonitriles via Lewis acid catalysed domino-ring-opening-cyclisation (DROC) of donor–acceptor cyclopropanes with malononitrile

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