Asymmetric Synthesis of Ring Functionalizedtrans-2,6-Disubstituted Piperidines fromN-Sulfinyl δ-Amino β-Keto Phosphonates. Total Synthesis of (−)-Myrtine
- 17 February 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 72 (6), 2046-2052
- https://doi.org/10.1021/jo062365t
Abstract
Sulfinimine-derived N-sulfinyl δ-amino β-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.Keywords
This publication has 69 references indexed in Scilit:
- Asymmetric Synthesis of 2,4,5-Trisubstituted Piperidines from Sulfinimine-Derived δ-Amino β-Ketoesters. Formal Synthesis of Pseudodistomin B TriacetateThe Journal of Organic Chemistry, 2005
- Enantioselective Synthesis of Piperidine, Indolizidine, and Quinolizidine Alkaloids from a Phenylglycinol-Derived δ-LactamThe Journal of Organic Chemistry, 2003
- A New Horner−Wadsworth−Emmons Type Coupling Reaction between Nonstabilized β-Hydroxy Phosphonates and Aldehydes or KetonesJournal of the American Chemical Society, 2003
- Indolizidine and quinolizidine alkaloids (July 1999 to June 2000)Natural Product Reports, 2001
- Synthesis of (−)-Lasubine(I) via a Planar Chiral [(η6-arene)Cr(CO)3] ComplexOrganic Letters, 1999
- Efficient Total Synthesis of Enantiopure (−)-PorantheridineThe Journal of Organic Chemistry, 1999
- Naturally Occurring Proline AnaloguesJournal of Natural Products, 1996
- Dephosphonylation of β-Keto Phosphonates with LiAlH4The Journal of Organic Chemistry, 1996
- Asymmetric synthesis of (-)-porantheridineJournal of the American Chemical Society, 1993
- Chemoenzymatic preparation of trans-2,6-dialkylpiperidines and of other azacycle building blocks. Total synthesis of (+)-desoxoprosopinineJournal of the American Chemical Society, 1989