A short enantioselective access to 2,3,6-trialkylpiperidines and 5,8- dialkylindolizidines

Tetrahedron

Volumn 54, Issue 32, 1998, Pages 9357-9372

  Wong, Yung Sing ^a   Gnecco, Dino ^b   Marazano, Christian ^a   Chiaroni, Angèle ^a   Riche, Claude ^a   Billion, Annick ^a   Das, Bhupesh C ^a  

^a CNRS   (France)

^b BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

Author keywords

[No Author keywords available]

Indexed keywords

8 ETHYL 5 PROPYLOCTAHYDROINDOLIZIDINE; INDOLIZIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0032490919     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00566-3     Document Type: Article

References (18)

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3. (c) Gnecco, D.; Marazano, C.; Das, B. C. J. Chem. Soc. Chem. Commun. 1991, 625;
4. (d) For related examples of use of chiral 1,4-dihydropyridine equivalents obtained from (R)-(-)-phenylglycinol see: Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670; Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475.
5. (d) For related examples of use of chiral 1,4-dihydropyridine equivalents obtained from (R)-(-)-phenylglycinol see: Royer, J.; Husson, H.-P. J. Org. Chem. 1985, 50, 670; Grierson, D. S.; Royer, J.; Guerrier, L.; Husson, H.-P. J. Org. Chem. 1986, 51, 4475.
6. H-8a, H-8 = 2.6 Hz) at 3.82 ppm. Accordingly, a 5R, 8S, 8aS configuration can be proposed for this unstable intermediate.
7. 3. GC analyses were performed on a capillary column after derivatization of the alcoholic functions as t-butyldimethylsilyl groups.
8. 4. Mohamadi, F.; Richards, N.J.G.; Guida, W.C.; Liskamp, R.; Lipton, M.C.; Caufield, M.; Chang, G.; Hendrickson, T.; Still, W.C. J. Comput. Chem. 1990, 11, 440.
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11. (b) Toyooka, N.; Tanaka, K., Momose, T.; Daly, J. W.; Garraffo, M. Tetrahedron 1997, 28, 9553;
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14. 8. For a useful discussion of the stereoselectivity of nucleophilic attack on related iminium ions see: Stevens, R. V. Acc. Chem. Res. 1984, 17, 289.
15. 2, and thus preferred to purify these compounds as HCl salts (see experimental).
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