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2005
Amination
O 0268
31- 053
Preparation of Enamides via Palladium-Catalyzed Amidation of Enol Tosylates.
— The procedure is applicable to enol tosylates bearing an aryl substituent or an electron-withdrawing group in the β-position of the double bond. A significant degree of
steric hindrance is tolerated in the enol tosylate providing a convenient method for the
synthesis of functionalized trisubstituted and tetrasubstituted enamides. An aryl group
at the α-position of the enol tosylate has a negative effect on the reaction, exemplified
by the lack of reactivity of substrates (XXIV). The positive effect of a β-phenyl group
is completely offset by the negative effect of the α-phenyl substituent in substrate
(XXV). Tosylate (XXVI) is unreactive as well. — (KLAPARS*, A.; CAMPOS, K. R.;
CHEN, C.-Y.; VOLANTE, R. P.; Org. Lett. 7 (2005) 6, 1185-1188; Dep. Process
Res., Merck Res. Lab., Merck&Co., Inc., Rahway, NJ 07065, USA; Eng.) —
R. Steudel
2005
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