DIASTEREOSELECTIVE SYNTHESIS OF HIGHLY FUNCTIONALIZED HOMOALLYLIC AMINE DERIVATIVES VIA DIELS-ALDER ADDUCTS OF N-SULFINYL DIENOPHILES

Article abstract of DOI:10.1016/S0040-4020(01)90588-5

Novel methodology for the diastereoselective synthesis of some branched functionalized homoallylic amine derivatives is described.The protocol starts with a 3,6-dihydrothiazine-1-oxide, which is readily obtained in a totally stereospecific manner by the hetero-Diels-Alder cycloaddition of an N-sulfinyl dienophile and a 1,3-diene.Various Grignard reagents have been added to these adducts to afford sulfoxide derivatives which have been manipulated stereoselectively via <2,3>-or <3,3>-sigmatropic rearrangements into branched homoallylic amines potentially useful for further synthetic transformations.