Palladium-Catalyzed Cyclization Reactions of Acetylene-Containing Amino Acids

✍ Scribed by Larissa B. Wolf; Kim C. M. F. Tjen; Hefziba T. ten Brink; Richard H. Blaauw; Henk Hiemstra; Hans E. Schoemaker; Floris P. J. T. Rutjes

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 205 KB
• Volume: 344
• Category: Article
• ISSN: 1615-4150
• DOI: 10.1002/1615-4169(200201)344:1<70::aid-adsc70>3.0.co;2-1

✦ Synopsis

Enantiomerically pure acetylene-containing aamino acids were used as versatile starting materials for the synthesis of a variety of heterocycles via Pd-mediated cyclization reactions. Depending on the protecting group strategy, both the carboxylate and the amine function of the amino acids could participate in the cyclizations, thus giving rise to oxygen heterocycles (a-aminolactones) and nitrogen heterocycles (cyclic a-amino acid derivatives), respectively.

Beside the straightforward cyclization, cyclization/crosscoupling reactions were also successfully carried out to provide the corresponding substituted cyclic amino acid derivatives.