Two-directional carbon chain elongation via the consecutive 1,4-addition of allyl malononitrile and the Cope rearrangement on an alkynoate platform

A one-pot procedure for the regioselective introduction of two different three-carbon units, allyl and malononitrile functionalities, to C-C triple bonds was established. The transformation proceeds through the phosphine-catalyzed 1,4-addition of allyl malononitrile to the alkynoate and the Cope rearrangement with microwave heating, achieving two-directional carbon chain elongation on the alkynoate platform. The operational simplicity, succinct carbon skeletal construction, and high atom economy should make the present procedure appealing for the synthesis of structurally complex organic molecules. (C) 2015 Elsevier Ltd. All rights reserved.