☆ 4.8 Article

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

ORGANIC LETTERS (2015)

Journal

ORGANIC LETTERS

Volume 17, Issue 2, Pages 322-325

Publisher

AMER CHEMICAL SOC

DOI: 10.1021/ol503432b

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Categories

Chemistry, Organic

Funding

Natural Science and Engineering Research Council (NSERC) of Canada
Universite de Sherbrooke
Center in Green Chemistry and Catalysis (CGCC) fellowship

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Abstract

beta-Amino acids are routinely incorporated into peptidic drugs to increase their stability and to incur conformational biases. However, the synthesis of highly substituted beta-amino acids still represents a great challenge. A new approach to their preparation is reported involving a VilsmeierHaack reaction with nonaromatic carbon nucleophiles. The highly challenging preparation of contiguous tertiary and all-carbon quaternary centers was successfully used to generate several beta(2,2,3)-amino esters, such as derivatives of homoproline, homoalanine, and homopipecolinic esters.

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