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  • Expedient preparation of all isomers of 2-aminocyclobutanecarboxylic acid in enantiomerically pure form.

Expedient preparation of all isomers of 2-aminocyclobutanecarboxylic acid in enantiomerically pure form.

The Journal of organic chemistry (2009-03-17)
Carlos Fernandes, Elisabeth Pereira, Sophie Faure, David J Aitken
ABSTRACT

A short, convenient, gram scale protocol has been established to allow facile access to all four stereoisomers of 2-aminocyclobutanecarboxylic acid, each in enantiomerically pure form (ee >99%). Starting from the readily available cis racemate, the procedure combines efficient alpha-phenylethylamine derivative resolution and controlled cis-to-trans epimerization procedures, and proceeds with invariably high yields.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(R)-(+)-α-Methylbenzylamine, purum, ≥98.0% (sum of enantiomers, GC)
Sigma-Aldrich
α-Methylbenzylamine, 99%
Sigma-Aldrich
(R)-(+)-α-Methylbenzylamine, 98%
Sigma-Aldrich
(R)-(+)-α-Methylbenzylamine, ChiPros®, produced by BASF, ≥99.0%
Sigma-Aldrich
(S)-(−)-α-Methylbenzylamine, 98%
Sigma-Aldrich
(S)-(−)-α-Methylbenzylamine, ChiPros®, produced by BASF, ≥99.0%