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DBU-Catalyzed Rearrangement of Secondary Propargylic Alcohols: An Efficient and Cost-Effective Route to Chalcone Derivatives

Rimpa De, Antony Savarimuthu, Tamal Ballav, Pijush Singh, Jayanta Nanda, Avantika Hasija, Deepak Chopra, Mrinal K. Bera*

*Department of Chemistry, Indian Institute of Engineering Science and Technology (IIEST), Shibpur, P.O - Botanic Garden, Howrah - 711 103 (WB), India, Email: mrinalkbera26gmail.com

R. De, A. Savarimuthu, T. Ballav, P. Singh, J. Nanda, A. Hasija, D. Chopra, M. K. Bera, Synlett, 2020, 31, 1587-1592.

DOI: 10.1055/s-0040-1707909 (free Supporting Information)


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Abstract

DBU catalyzes a rearrangement of diarylated secondary propargylic alcohols to give α,β-unsaturated carbonyl compounds in excellent yields. The typical 1,3-transposition of oxy functionality, characteristic of Meyer-Schuster rearrangements, is not observed. This method offers a broad substrate scope, functional-group tolerance, operational simplicity, and complete atom economy.

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Key Words

rearrangement, propargylic alcohols, DBU, enones, chalcones, allenols, organocatalysis


ID: J72-Y2020