Diastereoselective synthesis of highly functionalized homoallylic amine derivatives via diels-alder adducts of N-sulfinyl dienophiles

Ravi S. Garigipati, Robert Cordova, Masood Parvez, Steven M. Weinreb

Research output: Contribution to journalArticle

23 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)2979-2983
Number of pages5
JournalTetrahedron
Volume42
Issue number11
DOIs
StatePublished - Jan 1 1986

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sulfoxide
Amines
Derivatives
Cycloaddition
Cycloaddition Reaction
Oxides

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Garigipati, Ravi S. ; Cordova, Robert ; Parvez, Masood ; Weinreb, Steven M. / Diastereoselective synthesis of highly functionalized homoallylic amine derivatives via diels-alder adducts of N-sulfinyl dienophiles. In: Tetrahedron. 1986 ; Vol. 42, No. 11. pp. 2979-2983.
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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.

In: Tetrahedron, Vol. 42, No. 11, 01.01.1986, p. 2979-2983.

Research output: Contribution to journalArticle

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