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2004
Amines
Q 0120
48- 073
Synthesis of Enamides from Aldehydes and Amides. — An efficient route to doubly unsaturated amides (VI) and (VII) using cross-coupling of aldehydes with amides
and conversion of N-acylated hemiacetals to the desired enamides as key steps is reported. Heating the hemiaminals (III) in the presence of Ac2O and pyridine affects clean
conversion to the corresponding enamides (VI) and (VII) favoring the E-isomer. In contrast base-induced elimination of the corresponding sulfones (VIII) and in situ prepared
mesylates leads preferentially to the Z-isomers (VII). — (BAYER, A.; MAIER*, M.
E.; Tetrahedron 60 (2004) 31, 6665-6677; Inst. Org. Chem., Eberhard-Karls-Univ.,
D-72076 Tuebingen, Germany; Eng.) — Bartels
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