Tetrahedron p. 2979 - 2984 (1986)
Update date:2022-07-30
Topics:
Garigipati, Ravi S.
Cordova, Robert
Parvez, Masood
Weinreb, Steven M.
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.
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Doi:10.1246/cl.1986.2109
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(1988)
