Abstract
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.
Original language | English (US) |
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Pages (from-to) | 2979-2983 |
Number of pages | 5 |
Journal | Tetrahedron |
Volume | 42 |
Issue number | 11 |
DOIs | |
State | Published - 1986 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry