Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine
- PMID: 17305397
- PMCID: PMC2597462
- DOI: 10.1021/jo062365t
Asymmetric synthesis of ring functionalized trans-2,6-disubstituted piperidines from N-sulfinyl delta-amino beta-keto phosphonates. total synthesis of (-)-myrtine
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.
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References
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During a 10-year period Watson and co-workers state that there were thousands of piperidine compounds cited in clinical and preclinical trials. Watson PS, Jiang B, Scott B. Org Lett. 2000;2:3679.
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- Leclercq S, Braekman JC, Daloze D, Pasteels JM. Prog Chem Org Nat Prod. 2000;79:115. - PubMed
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For leading references see: Davis BG, Maughan MAT, Chapman TM, Villard R, Courtney S. Org Lett. 2002;4:103.Davis BG. Chem Rev. 2002;102:579.
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