Organic letters

Regioselective Heck couplings of α, β-unsaturated tosylates and mesylates with electron-rich olefins

AL Hansen, T Skrydstrup

Index: Hansen, Anders Lindhardt; Skrydstrup, Troels Organic Letters, 2005 , vol. 7, # 25 p. 5585 - 5587

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Citation Number: 76

Abstract

Highly regioselective Heck couplings of α, β-unsaturated tosylate and mesylate derivatives with N-acyl N-vinylamines and vinyl ethers were achieved. Several 2-alkoxy-1, 3-dienes and 2-acylamino-1, 3-butadienes were synthesized in good yields using 1.5 mol% of Pd2 (dba) 3, 3 mol% of DPPF, and diisopropylethylamine in dioxane. When working with α, β- unsaturated ketones and esters, this method provides a less costly alternative to similar ...