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Efficient synthesis of symmetrical alpha,alpha-disubstituted beta-amino acids and alpha,alpha-disubstituted aldehydes via dialkylation of nucleophilic beta-alanine equivalent

Efficient synthesis of symmetrical alpha,alpha-disubstituted beta-amino acids and alpha,alpha-disubstituted aldehydes via dialkylation of nucleophilic beta-alanine equivalent

Journal of Organic Chemistry 75(5): 1717-1722

Homologation of the nucleophilic beta-alanine equivalent beta-Ala Ni(II)-PABP [Ni(II) complex of beta-alanine Schiff base with 2-[N-(alpha-picolyl)amino]benzophenone (PABP), 1] via alkyl halide alkylation was systematically studied as a general method for preparing symmetrically alpha,alpha-disubstituted beta-amino acids. The dialkylation reactions could be easily performed and did not require inert atmosphere, dried solvents, and low temperatures, thereby affording the benefits of operationally convenient experimental procedure and high atom economy. Further, the methodology developed by us can also be used to generate symmetrical alpha,alpha-disubstituted aldehydes through an alternative decomposition method.

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Accession: 052911330

Download citation: RISBibTeXText

PMID: 20141112

DOI: 10.1021/jo902699t

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