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Preparation of Conformationally Restricted β2,2- and β2,2,3-Amino Esters and Derivatives Containing an All-Carbon Quaternary Center

Alexandre Romanens and Guillaume Bélanger*

*Département de Chimie, Université de Sherbrooke, 2500 boulevard de l’Université, Sherbrooke, Québec J1K 2R1, Canada, Email: Guillaume.BelangerUSherbrooke.ca

A. Roamens, G. Bélanger, Org. Lett., 2015, 17, 322-325.

DOI: 10.1021/ol503432b (free Supporting Information)


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Abstract

A preparation of highly substituted β-amino acids involves a Vilsmeier-Haack reaction with nonaromatic carbon nucleophiles. The reaction enabled the synthesis of several β2,2,3-amino esters, such as derivatives of homoproline, homoalanine, and homopipecolinic esters.

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Key Words

β-amino esters, sodium cyanoborohydride, sodium triacetoxyborohydride


ID: J54-Y2015