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Asymmetric syntheses of (S,S,S)-2-amino-5-methylcyclopentanecarboxylic acid and (S,S,S)-2-amino-5-phenylcyclopentanecarboxylic acid were achieved in 9 steps from commercially available starting materials via the Ireland-Claisen rearrangement of two enantiopure β-amino allyl esters, followed by ring-closing metathesis, reduction and deprotection.

Original publication

DOI

10.1039/c3cc43250e

Type

Journal article

Journal

Chem Commun (Camb)

Publication Date

14/08/2013

Volume

49

Pages

7037 - 7039

Keywords

Carboxylic Acids, Crystallography, X-Ray, Cycloleucine, Molecular Conformation, Oxidation-Reduction, Stereoisomerism