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 Scopus citations

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

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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