The Bimolecular Aromatic Mannich Reaction
1991; Elsevier BV; Linguagem: Inglês
10.1016/b978-0-08-052349-1.00053-6
Autores Tópico(s)Asymmetric Synthesis and Catalysis
ResumoThe importance of α-aminoalkylation as a method of carbon–carbon bond formation has been recognized for many years, especially among those organic chemists interested in biologically active molecules. The earliest papers were published towards the end of the last century but Mannich was the first to recognize the generality of the reaction and his first paper appeared over 75 years ago. A number of reviews1 and two books2 record data up to 1973. The importance of the Mannich reaction relates in part to the fact that the protonated bases are normally water soluble and also to the ease with which the amino function may be converted into a variety of other groups. New examples continue to be published. For example, the nuclear ortho methylation of phenols has been reported via the reduction of Mannich bases and their quaternary methiodides and N-oxides using tributyltin hydride;3a sodium cyanoborohydride has also been used.3b Chapter 4.1 is concerned with aliphatic bimolecular Mannich reactions, while this chapter deals with intermolecular reactions of Mannich reagents with aromatic substrates. This chapter concentrates on recent advances in synthetic methodology
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