Brønsted Acid-Catalyzed Epimerization-Free Preparation of Dual-Protected Amino Acid Derivatives | Zendy

Pedro P. de Castro | Zendy; Isabela M. R. Rimulo | Zendy; Angelina M. de Almeida | Zendy; Renata Diniz | Zendy; Giovanni W. Amarante | Zendy

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Brønsted Acid-Catalyzed Epimerization-Free Preparation of Dual-Protected Amino Acid Derivatives

Author(s) -

Pedro P. de Castro,

Isabela M. R. Rimulo,

Angelina M. de Almeida,

Renata Diniz,

Giovanni W. Amarante

Publication year - 2017

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.7b00523

Subject(s) - epimer , racemization , chemistry , electrospray ionization , nucleophile , amine gas treating , catalysis , mass spectrometry , brønsted–lowry acid–base theory , amino acid , organic chemistry , organocatalysis , combinatorial chemistry , chromatography , enantioselective synthesis , biochemistry

An organocatalytic protocol, employing the commercially available EDC as coupling agent, has been developed for the preparation of dual-protected amino acid derivatives without epimerization. This methodology was then applied to different Boc-amino acid and amine derivatives in moderate to excellent isolated yields. In addition, racemization-free Boc deprotection was also demonstrated. Mechanism investigation through electrospray ionization (+)-mass spectrometry/mass spectrometry revealed an acyclic intermediate (no azlactone formation) activated by the camphorsulfonic acid as an organocatalyst as a key step for the sequential attack of the nucleophile.

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