Efficient multicomponent reaction for the synthesis of piperidine derivatives: Yb(OTf)3/AgOTf cocatalyzed preparation of trimethyl 3,5,5-piperidonetricarboxylate

Synthetic Communications

Volumn 38, Issue 24, 2008, Pages 4321-4327

  Lian, Gao Yan ^a   Lin, Feng ^a   Yu, Jin Di ^a   Zhang, Dan Wei ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Cocatalyst; Multicomponent reaction; Piperidine derivatives

Indexed keywords

AMINO ACID; DIMETHYL MALONIC ACID; FORMALDEHYDE; MALONIC ACID DERIVATIVE; OXIME; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE; SILVER; TRICARBOXYLIC ACID; TRIMETHYL 3,5,5 PIPERIDONETRICARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG; YTTERBIUM;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 57349123552     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910802323122     Document Type: Article

References (17)

1. 1 subunit. Bioorg. Med. Chem. Lett. 2000, 10, 1381-1384.
2. Kim, B. M.; Shaw, A. W.; Graham, S. L.; de Solms, J. S.; Ciccarone, T. M. Inhibitors of farnesyl-protein transferase. US Patent 5,817,678, Oct. 6, 1998.
3. (a) Angenot, L.; Diberg, O.; Dupont, L. Isolation and structure of akagerine: A new type of indole alkaloid. Tetrahedron Lett. 1975, 16, 1357-1358;
4. (b) Pouilhès, A.; Langlois, Y. Preparation of 7-methoxy-3,4- dihydro-β-carboline. Heterocycles 1981, 15, 935-941.
5. (a) Buffat, M. G. P. Synthesis of piperidines. Tetrahedron 2004, 60, 1701-1729;
6. (b) Felpin, F.-X.; Lebreton, J. Recent advances in the total synthesis of piperidine and pyrrolidine natural alkaloids with ring-closing metathesis as a key step. Eur. J. Org. Chem. 2003, 3693-3712;
7. (c) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Recent advances in the synthesis of piperidones and piperidines. Tetrahedron 2003, 59, 2953-2989.
8. Park, J.-S.; Yeom, C.-E.; Choi, S. H.; Ahn, Y. S.; Ro, S.; Jeon, Y. H.; Shin, D.-K.; Kim, B. M. An efficient synthesis of 3(S)-aminopiperidine- 5(R)-carboxylic acid as a cyclic β,γ′-diamino acid. Tetrahedron Lett. 2003, 44, 1611-1614.
9. A literature survey revealed that only one case of similar compound synthesis in low yield has previously been reported. See Darnrrough, G.; Knowles, P.; Oconnor, S. P.; Tierney, J. New reactions of 1,3,5-trialkyl- hexahydro-1,3,5-triazines, part 1: The formatin of 3,7-diazabicyclo[3.3.1]nona- 2,6-diones and hexahydropyrimidines using activatated acetates. Tetrahedron 1986, 42, 2339-2344.
10. (a) Maligres, P. E.; Chartrain, M. M.; Upadhyay, V.; Cohen, D.; Reamer, R. A.; Askin, D.; Volante, R. P.; Reider, P. J. Preparation of (S)-3-carbethoxy-3-benzylpiperidine and the growth hormone secretagogue L-163,540. J. Org. Chem. 1998, 63, 9548-9551;
11. (b) Askin, D.; Maligres, P.; Chartrain, M.; Volante, R. Process for the preparation of (S)-3-carbethoxy-3-benzylpiperidine. U.S. Patent 5929243, July 27, 1999;
12. (c) Schultz, A. G.; Lucci, R. D.; Napier, J. J.; Kinoshita, H.; Ravichandran, R.; Shannon, P.; Yee, Y. K. Studies directed at a synthesis of the morphine alkaloids: A photochemical approach. J. Org. Chem. 1985, 50, 217-231.
13. 12-dependent methylitaconate ↔ α-methyleneglutarate model rearrangement reaction and examination of potential cyclopropane intermediates. J. Chem. Soc., Perkin Trans. 2, 1988, 61-70.
14. Gogoll, A.; Johansson, C.; Axén, A.; Grennberg, H. Determination of absolute configuration of (π-allyl)palladium complexes by NMR spectroscopy and stereoselective complexation. Chem. Eur. J. 2001, 7, 396-403.
15. (a) Hearn, M. T. W.; Ward, A. D. Hydroxamic acids, VI: The synthesis, properties, and reactions of amidic hydroxamic acid and dihydroxamic acid derivatives. Austr. J. Chem. 1977, 30, 2031-2043;
16. (b) Strazzolini, P.; Pavsler, A. Highly efficient, low-cost, and simple protocol for the preparation of O-(phenylmethyl)hydroxylamine. Ind. Eng. Chem. Res. 2005, 44, 1625-1626;
17. (c) Ikeda, K.; Achiwa, K.; Sekiya, M. A convenient synthesis of N-benzyloxy-β-lactams via N-benzyloxyimines. Chem. Pharm. Bull. 1989, 37, 1179-1184.