Abstract
In solid-phase organic synthesis, Wang resin is traditionally used for the immobilization of acids, alcohols, phenols, and amines. We report the use of Wang resin for the traceless synthesis of ketones via acid-labile enol ethers. We demonstrate the practicality of this synthetic strategy on the solid-phase synthesis of pyrrolidine-2,4-diones, which represent the core structure of several natural products, including tetramic acid. Base-triggered condensation of pyrrolidine-2,4-diones yielded 4-hydroxy-1,1′,2′,5-tetrahydro-2H,5′H-[3,3′-bipyrrole]-2,5′-diones.
Highlights
Solid-phase synthesis is a very attractive methodology for the time-efficient synthesis of diverse organic molecules [1,2,3,4]
After finishing the synthesis, the product is released from the resin and the functional group that was initially used for immobilization will remain attached to the product
We expand the application of Wang resin to the novel, traceless synthesis of ketones from acid-labile enol ethers, which were prepared via the Wittig reaction of resin-bound esters
Summary
Solid-phase synthesis is a very attractive methodology for the time-efficient synthesis of diverse organic molecules [1,2,3,4]. Enol ethers represent valuable synthons in organic synthesis, and numerous methods for the synthesis of enol ethers have been reported; the Wittig olefination of esters is used rarely [9]. This ’nonclassical’ Wittig reaction of carboxylate esters suffers from sluggish reactivity due to the low electrophilicity of the carbonyl carbon towards phosphoranes compared to the electrophilicity of aldehydes and ketones [10]. We report a simple and practical synthesis of acid-labile Wang resin-bound enol ethers via the Wittig olefination of carboxylate esters and subsequent acid-mediated traceless release of the ketones from the resin
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