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An unexpected rearrangement of a ß-amino sulfoxide under pummerer reaction conditions

Journal Article


Abstract


  • Attempts to prepare the benzazepine ring system of the Rhoedine alkaloids using a Pummerer cyclization of the β-amino sulfoxide (16) gave instead the unexpected alcohol (19). The β-amino sulfoxide (16) was prepared via a diastereoselective reduction of the β-sulfinyl enamine (8) with sodium borohydride. © 1994.

Publication Date


  • 1994

Citation


  • G. Pyne, S., & Hajipour, A. R. (1994). An unexpected rearrangement of a ß-amino sulfoxide under pummerer reaction conditions. Tetrahedron, 50(47), 13501-13510. doi:10.1016/S0040-4020(01)89357-1

Scopus Eid


  • 2-s2.0-0027948278

Web Of Science Accession Number


Start Page


  • 13501

End Page


  • 13510

Volume


  • 50

Issue


  • 47

Abstract


  • Attempts to prepare the benzazepine ring system of the Rhoedine alkaloids using a Pummerer cyclization of the β-amino sulfoxide (16) gave instead the unexpected alcohol (19). The β-amino sulfoxide (16) was prepared via a diastereoselective reduction of the β-sulfinyl enamine (8) with sodium borohydride. © 1994.

Publication Date


  • 1994

Citation


  • G. Pyne, S., & Hajipour, A. R. (1994). An unexpected rearrangement of a ß-amino sulfoxide under pummerer reaction conditions. Tetrahedron, 50(47), 13501-13510. doi:10.1016/S0040-4020(01)89357-1

Scopus Eid


  • 2-s2.0-0027948278

Web Of Science Accession Number


Start Page


  • 13501

End Page


  • 13510

Volume


  • 50

Issue


  • 47