An Effective Synthesis of (±)-(E)-2-Amino-5-phosphono-3-pentenoic Acid by Palladium(II)-assisted Migration of the Double Bond
Year: 1990
Type: article
Abstract: A new approach for the synthesis of (±)-(E)-2-amino-5-phosphono-3-pentenoic acid (E-APPA) is described. The key intermediate, (E)-5-acetoxy-3,4-dehydronorvaline derivative 8, was prepared by [3,3]-sigmatropic rearrangement of allyl acetate 7 in the presence of Pd(II) catalyst. The acetoxy group in 8 was transformed into the phosphonyl group to furnish (E)-APPA in a moderate yield.
Authors: Mitsunori Kirihata, Seiichi Kawahara, Itsuo Ichimoto, Hiroo Ueda
Institution: Osaka Prefecture University
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
OpenAlex ID: W2331960035