Intramolecular cycloaddition of the azomethine ylides derived from α-amino acids or esters and 5-Oxo-6-heptenals or 4-Oxo-5-hexenals

Article abstract of DOI:10.1246/bcsj.63.2866

Intramolecular cycloadditions of the azomethine ylides bearing a carbonyl-activated olefinic moiety, generated from a-amino acids or esters and 5-oxo-6-heptenals or 4-oxo-5-hexenals, produce the stereoselective internal cycloadducts either to olefin or carbonyl dipolarophilic function with normal or inverse regioselectivity, depending upon the types of ylides as well as the intervening chain length. Exclusively high diastereofacial selectivity has been achieved when 2-phenyl-4-thiazolidinecarboxylic acid and its methyl ester are utilized.