Tetrahedron Letters

Traceless sulfone linker cleavage triggered by ozonolysis: solid-phase synthesis of diverse α-β-unsaturated carbonyl compounds

YF Chang, YR Jiang, WC Cheng

Index: Chang, Yi-Fan; Jiang, Yi-Rui; Cheng, Wei-Chieh Tetrahedron Letters, 2008 , vol. 49, # 3 p. 543 - 547

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Citation Number: 15

Abstract

The highly efficient and convenient protocol to prepare diverse α, β-unsaturated aldehydes, ketones, and acids via the parallel solid-phase synthesis is developed. The key sulfone linker cleavage strategy is performed by ozonolysis to generate a carbonyl moiety followed by base-mediated polymer-bound sulfinate elimination to release our desired molecules from the resin. All α, β-unsaturated carbonyl compounds are prepared in good purities and ...