Journal
TETRAHEDRON LETTERS
Volume 57, Issue 1, Pages 137-140Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2015.11.081
Keywords
Phosphine catalyst; 1,4-Addition; Cope rearrangement; Microwave; Alkynoate
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Funding
- Program to Disseminate Tenure Tracking System (MEXT, Japan)
- Grants-in-Aid for Scientific Research [26105741] Funding Source: KAKEN
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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.
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