Brønsted Acid-Catalyzed Epimerization-Free Preparation
of Dual-Protected Amino Acid Derivatives
Version 2 2017-06-27, 15:24
Version 1 2017-06-27, 15:18
Posted on 2017-06-27 - 15:24
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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de Castro, Pedro
P.; Rimulo, Isabela M. R.; de Almeida, Angelina M.; Diniz, Renata; Amarante, Giovanni W. (2017). Brønsted Acid-Catalyzed Epimerization-Free Preparation
of Dual-Protected Amino Acid Derivatives. ACS Publications. Collection. https://doi.org/10.1021/acsomega.7b00523
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AUTHORS (5)
Pd
Pedro
P. de Castro
IR
Isabela M. R. Rimulo
Ad
Angelina M. de Almeida
RD
Renata Diniz
GA
Giovanni W. Amarante