Diastereoselectivity in the addition and cycloaddition reactions of a chiral ester of 2H-azirine-3-carboxylic acid
Abstract
The Azirine ester 2 bearing Oppolzer’s N,N-diethyl-(1R)-isobornyl-10-sulfonamide chiral auxilliary shows moderate diastereoselectivity in its Diels-Alder reaction with cyclo-pentadiene whereas the addition of thiophenol is highly diastereoselective; X-ray crystal structures of the aziridine esters 6 and 7 are reported.