Palladium-Mediated Intramolecular Aryl Animation on Furanose Derivatives:An Expedient Approach to the Synthesis of Chiral Benzoxazocine Derivatives and Tricyclic Nucleosides

摘要

Pd-catalyzed intramolecular arylamination on sugar derivatives has been accomplished by using bulky biaryl phosphine ligands.An application of this methodology on a variety of D-glucose-derived substrates,2a-f,led to the synthesis of highly functionalized cis-fused tricyclic oxazocines,3a-e.The products could subsequently be transformed to the optically active benzoxazocine derivative 4 and tricyclic nucleoside 6.This is the first example of the synthesis of eight-membered rings via intramolecular cycloamination of furanose derivatives,which provides a very useful method for the catalytic synthesis of medium-ring heterocycles.