107972-73-6Relevant academic research and scientific papers
DIASTEREOSELECTIVE SYNTHESIS OF HIGHLY FUNCTIONALIZED HOMOALLYLIC AMINE DERIVATIVES VIA DIELS-ALDER ADDUCTS OF N-SULFINYL DIENOPHILES
Garigipati, Ravi S.,Cordova, Robert,Parvez, Masood,Weinreb, Steven M.
, p. 2979 - 2984 (2007/10/02)
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 -or -sigmatropic rearrangements into branched homoallylic amines potentially useful for further synthetic transformations.
