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Aza-Henry Reactions on C-Alkyl Substituted Aldimines.

ABSTRACT: The reactivity of C-CH? substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse electrophiles than C-CF? aldimines, they gave the aza-Henry addition only when ZrCl? was added. The presence of a bulky group on the imine carbon deeply influenced the reactivity.

SUBMITTER: Pelagalli A

PROVIDER: S-EPMC6273577 | biostudies-literature | 2016 Jun

REPOSITORIES: biostudies-literature

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Aza-Henry Reactions on C-Alkyl Substituted Aldimines.

Pelagalli Alessia A Pellacani Lucio L Scandozza Elia E Fioravanti Stefania S

Molecules (Basel, Switzerland) 20160602 6

The reactivity of C-CH₃ substituted N-protected aldimines in aza-Henry addition reactions was compared with that of the analogous trifluoromethylated compounds. C-Alkyl aldimines easily reacted with nitro alkanes under solvent-free conditions and in the absence of catalyst, despite being worse electrophiles than C-CF₃ aldimines, they gave the aza-Henry addition only when ZrCl₄ was added. The presence of a bulky group on the imine carbon deeply influenced the reactivity. ...[more]

PMID: 27271579

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