Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine.
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.
Davis
Franklin A
FA
Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. fdavis@temple.edu
Xu
He
H
Zhang
Junyi
J
D063065:Organophosphonates / Q000737:chemistry*; D010880:Piperidines / Q000138:chemical synthesis*; D011725:Pyridines / Q000737:chemistry; D011728:Pyridones / Q000737:chemistry; D011807:Quinolizines / Q000138:chemical synthesis*
D063065:Organophosphonates; D010880:Piperidines; D011725:Pyridines; D011728:Pyridones; D011807:Quinolizines; C519820:myrtine