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Updated: Jul 26, 2025

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Aminative annulation of cyano-enynyl esters leading to functionalized cyclopentenones
Chada Raji Reddy1, Veeramalla Ganesh1, Nagender Punna2
1Department of Organic Synthesis & Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500007, India. rajireddy@iict.res.in.
Abstract:
A base-mediated unexpected aminative carbo-cyclization of cyano-enynyl esters, generated from Morita-Baylis-Hillman (MBH) acetates of propiolaldehydes, with secondary-amines is described. This metal-free reaction allows the synthesis of a unique cyclopentenone bearing an exocyclic double bond (cyano-olefin) with high E-selectivity in good yields. The synthetic potential of this annulation was further exemplified by the derivatization of bioactive molecules, a scale-up synthesis and synthetic transformations of the obtained cyclopentenone.
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