Tetrahedron letters

α-Addition of activated methylenes to alkynoates. A straightforward synthesis of multifunctional compounds

M Hanédanian, O Loreau, F Taran, C Mioskowski

文献索引：Hanedanian, Mikael; Loreau, Olivier; Taran, Frederic; Mioskowski, Charles Tetrahedron Letters, 2004 , vol. 45, # 38 p. 7035 - 7038

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被引用次数: 37

摘要

The Michael addition of stabilized enolates with alkynoates constitutes a fundamental synthetic reaction, which normally yields C-conjugate Michael adducts. This classical reactivity can be circumvented by the addition of catalytic amount of N-methylmorpholine (NMM) or DABCO, which have been recently described to induce the formation of unusual O-conjugate Michael adducts 3 through the reactivity of ammonium intermediate 2 (Scheme 1). 1 On another hand, ...