Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine

J Org Chem. 2007 Mar 16;72(6):2046-52. doi: 10.1021/jo062365t. Epub 2007 Feb 17.

Abstract

Sulfinimine-derived N-sulfinyl delta-amino beta-ketophosphonates are transformed via the enaminones to the phosphoryl dihydropyridones that selectively give trans-2,6-disubstituted 1,2,5,6-tetrahydropyridines on organocuprate addition and dephosphorylation.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Organophosphonates / chemistry*
  • Piperidines / chemical synthesis*
  • Pyridines / chemistry
  • Pyridones / chemistry
  • Quinolizines / chemical synthesis*

Substances

  • Organophosphonates
  • Piperidines
  • Pyridines
  • Pyridones
  • Quinolizines
  • myrtine