ChemInform Abstract: Development of the Ireland—Claisen Rearrangement of Alkoxy- and Aryloxy-Substituted Allyl Glycinates.

✍ Scribed by James P. Tellam; David R. Carbery

• Publisher: John Wiley and Sons
• Year: 2011
• Weight: 47 KB
• Volume: 42
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.201110038

✦ Synopsis

Development of the Ireland-Claisen Rearrangement of Alkoxy-and Aryloxy--Substituted Allyl Glycinates. -The title rearrangement of glycinates of type (IV) allows a new and highly stereoselective access to syn-β-alkoxy-α-amino acid derivatives. The nature of N-substituents has strong influence on the stereochemical outcome. Starting from N-phthalimide substrates only few β-aryloxy-α-amino acid derivatives are available. Preferred formation of anti-isomers is also possible but only low selectivity can be achieved. -(TELLAM, J.