Stereoselective synthesis of chiral piperidine derivatives employing arabinopyranosylamine as the carbohydrate auxiliary

Canadian Journal of Chemistry

Volumn 84, Issue 4, 2006, Pages 625-641

  Kranke, Birgit ^a   Kunz, Horst ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Carbohydrate auxiliary; Conjugate cuprate and hydride addition; Domino Mannich Michael reaction; Electrophilic substitution of enamines; Piperidine alkaloids

Indexed keywords

ALKYLATION; CARBOHYDRATES; HALOGEN COMPOUNDS; NUCLEAR MAGNETIC RESONANCE; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

CARBOHYDRATE AUXILIARY; CONJUGATE CUPRATE AND HYDRIDE ADDITION; DOMINO MANNICH-MICHAEL REACTION; ELECTROPHILIC SUBSTITUTION OF ENAMINES; PIPERIDINE ALKALOIDS;

NITROGEN COMPOUNDS;

1,3 BUTADIENE; 2 METHYL 6 N PROPYLPIPERIDINE HYDROCHLORIDE (DIHYDROPINIDINE); 2 N PROPYLPIPERIDINE HYDROCHLORIDE; AMINE; ARABINOPYRANOSYLAMINE; CARBOHYDRATE DERIVATIVE; DEHYDROPIPERIDINE DERIVATIVE; ENAMINE; HALOGEN; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 (3 TERT BUTYLDIPHENYLSILOXY)PROPYL 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 (4 CHLOROPHENYL) 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 (4 CHLOROPHENYL) 6 PHENYLPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 (4 NITROPHENYL) 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 ALLYL 6 (4 CHLOROPHENYL) 6 PIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 ALLYL 6 N PROPYLPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 ETHYL 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 ISOPROPYL 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 METHYL 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 METHYL 6 N PROPYLPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 METHYL 6 N PROPYLPIPERIDINE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 N PROPYL 4 (1,3 DITHIOLAN 2 YL) 6 METHYLPIPERIDINE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 N PROPYL 4 (TRIFLUORMETHANSULFONYLOXY) 4,5 DEHYDROPIPERIDINE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 N PROPYL 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 N PROPYLPIPERIDINE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 PHENYL 5,6 DEHYDROPIPERIDIN 4 ONE; N (2',3',4' TRI O PIVALOYL ALPHA DEXTRO ARABINOPYRANOSYL) 2 PHENYL 6 N PROPYLPIPERIDIN 4 ONE; PALLADIUM; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; DRUG SYNTHESIS; DRUG TRANSFORMATION; MANNICH REACTION; MICHAEL ADDITION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 33745919528     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-060     Document Type: Article

References (24)

1. (a) J.W. Daly, H.M. Garraffo, and T.F. Spande. In The alkaloids - Chemistry and pharmacology. Vol. 43. Edited by G.A Cordell. Academic Press, San Diego. 1993. p. 185;
2. (b) J.W. Daly. Nat. Prod. 61, 162 (1998);
3. (c) J.W. Daly, H.M. Garraffo, and T.F. Spande. In Alkaloids - Chemical and biological perspectives. Vol. 13. Edited by S.W. Pelletier. Pergamon, New York. 1999. p. 1.
4. (a) P.D. Bailey, P.A. Millwood, and P.D. Smith. Chem. Commun. (Cambridge), 633 (1998);
5. (b) S. Laschat and T. Dickner. Synthesis, 1781 (2000);
6. (c) P.M. Weintraub, J.S. Sabol, J.M. Kane, and D.R. Borcherding. Tetrahedron, 59, 2953 (2003);
7. (d) S. Knauer, B. Kranke, L. Krause, and H. Kunz. Curr. Org. Chem. 8, 1739 (2004).
8. (a) H. Kunz and W. Pfrengle. Angew. Chem. Int. Ed. Engl. 28, 1067 (1989);
9. (b) M. Weymann, W. Pfrengle, D. Schollmeyer, and H. Kunz. Synthesis, 1151 (1997).
10. B. Kranke, D. Hebrault, M. Schultz-Kukula, and H. Kunz. Synlett, 671 (2004).
11. H. Kunz, W. Pfrengle, K. Rück, and W. Sager. Synthesis, 1039 (1991).
12. Y. Yamamoto. Angew. Chem. Int. Ed. Engl. 25, 947 (1986).
13. E.J. Corey and W. Boaz. Tetrahedron Lett. 26, 6019 (1985).
14. H. Gilman, R.G. Jones, and L.A. Woods. J. Org. Chem. 17, 1630 (1952).
15. S. Ciblat, P. Besse, V. Papastergiou, H. Veschambre, J.-L. Canet, and Y. Troin. Tetrahdron: Asymmetry, 11, 2221 (2000), and refs. therein.
16. K. Maruoka, K. Nonoshita, and H. Yamamoto. Tetrahedron Lett. 28, 5723 (1987).
17. (a) G. Zech and H. Kunz. Angew. Chem. Int. Ed. 42, 787 (2003);
18. (b) G. Zech and H. Kunz. Chem. Eur. J. 10, 4136 (2004).
19. (a) J.K. Stille. Angew. Chem. Int. Ed. Engl. 25, 508 (1986);
20. (b) M.A.J. Duncton and G. Pattenden. J. Chem. Soc. Perkin Trans. 1, 1235 (1999).
21. N. Miyaura and A. Suzuki. Chem. Rev. 95, 2457 (1995).
22. S. Danishefsky and T. Kitahara. J. Am. Chem. Soc. 96, 7807 (1974).
23. J.A. Murphy, F. Rasheed, S.J. Roome, K.A. Scott, and N. Lewis. J. Chem. Soc. Perkin Trans. 1, 2331 (1998).
24. L. Guerrier, J. Royer, D.S. Grierson, and H.-P. Husson. J. Am. Chem. Soc. 105, 7754 (1983).