Asymmetric carbon-carbon bond-forming reaction at the 2-position of a piperidine skeleton

Chirality

Volumn 15, Issue 1, 2003, Pages 89-94

  Kanda, Yasuhisa ^a   Onomura, Osamu ^a   Maki, Toshihide ^a   Matsumura, Yoshihiro ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Bisoxazoline; Carbon carbon formation; Catalytic asymmetric synthesis; Copper ion catalyzed; Dimethyl malonate; Optically active 2 piperidylacetate

Indexed keywords

ACETIC ACID DERIVATIVE; CARBON; COPPER ION; MALONIC ACID DERIVATIVE; OXAZOLINE DERIVATIVE; PIPERIDINE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; ELECTROCHEMISTRY; FOURIER TRANSFORMATION; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PIPERIDINES; STEREOISOMERISM;

EID: 0037214263     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10151     Document Type: Article

References (14)

1. Bailey PD, Millwood PA, Smith PD. Asymmetric routes to substituted piperidines. Chem Commun 1998;633-640.
2. Plunkett O, Sainsbury M. Pyridine and piperidine alkaloids. In: Rodd's chemistry of carbon compounds, 2nd ed., vol. 4. Amsterdam: Elsevier; 1998. p 365-421.
3. Laschat S, Dickner T, Stereoselective synthesis of piperidines. Synthesis 2000;1781-1813.
4. Shono T, Matsumura Y, Tsubata K, Uchida K. Synthesis of optically active piperidine and pyrrolidine alkaloids from 1/-lysine, L-ornithine, or L-proline using anodic oxidation as key steps. J Org Chem 1986;51: 2590-2592.
5. Wanner KT, Kaertner A. Asymmetric α-amidoalkylation. Synthesis of a-substituted piperidines of high enantiomeric purity. Heterocycles 1987;26:921-924.
6. Matsumura Y, Kanda Y, Shirai K, Onomura O, Maki T. A convenient method for synthesis of enantiomerically enriched methylphenidate from N-methoxycarbonylpiperidine. Org Lett 1999;1:175-178.
7. Matsumura Y, Kanda Y, Shirai K, Onomura O, Maki T. A convenient method for synthesis of optically active methylphenidate from N-methoxycarbanylpiperidine by utilizing electrochemical oxidation and Evans aldol-type reaction. Tetrahedron 2000;56:7411-7422.
8. Onomura O, Kanda Y, Nakamura Y, Maki T, Matsumura Y. Copper ion-catalyzed asymmetric carbon-carbon bond-forming reaction at the 2-position of a piperidine skeleton. Tetrahedron Lett 2002;43:3229-3231.
9. Shono T, Hamaguchi H, Matsumura Y. Electroorganic chemistry. XX. Anodic oxidation of carbamates. J Am Chem Soc 1975;97:4264-4268.
10. Shono T, Matsumura Y, Tsubata K. Electrochemical oxidation of N-carbomethoxypyrrolidine: 2-Methoxy-N-carbomethoxypyrrolidine. Org Synth Coll Vol VII 1990;307-312.
11. Shono T, Matsumura Y, Tsubata K. Electroorganic chemistry. 46. A new carbon-carbon bond forming reaction at the a-position of amines utilizing anodic oxidation as a key step. J Am Chem Soc 1981;103:1172-1176.
12. Shono T, Matsumura Y, Ogaki M, Onomura O. Electroorganic chemistry. 109. A new method for introducing some active methylene or methine groups to the 3-position of pyrrolidine or piperidine skeleton, and its application to preparation of a key intermediate for (±) eburnamonine synthesis. Chemlett 1987;1447-1450.
13. Shono T, Matsumura Y, Onomura O, Yamada Y. Electroorganic chemistry. 108. A new method for regioselective synthesis of 2-substituted 1-(methoxycarbonyl)-1,2-dihydropyridines. Tetrahedron Lett 1987;28: 4073-4074.
14. Johnson JS, Evans DA. Chiral Bis(oxazoline) Copper(II) complexes: Versatile catalysts for enantioselective cycloaddition, aldol, Michael, and carbonyl ene reactions. Acc Chem Res 2000;33:325-335.