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  • Title: Stereoselective beta-hydroxy-alpha-amino acid synthesis via an ether-directed, palladium-catalysed aza-Claisen rearrangement.
    Author: Fanning KN, Jamieson AG, Sutherland A.
    Journal: Org Biomol Chem; 2005 Oct 21; 3(20):3749-56. PubMed ID: 16211111.
    Abstract:
    A highly diastereoselective synthesis of (2S,3S)-beta-hydroxy-alpha-amino acids has been developed from enantiopure alpha-hydroxy acids using a MOM-ether-directed, palladium(II)-catalysed, aza-Claisen rearrangement of allylic acetimidates to effect the key step. This highly stereoselective process gave allylic amides in diastereomeric ratios of up to 14 : 1. Problems associated with the isolation of 1,3-products (anti-Claisen) from sterically demanding substrates via an insitu palladium(0)-catalysed rearrangement process were overcome by the addition of a re-oxidant, p-benzoquinone, leading to cleaner reactions and improved yields of the 3,3-products (Claisen). The target beta-hydroxy-alpha-amino acids are an important class of natural products that are also components of more complex organic compounds with significant biological properties.
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