Stereoselective synthesis of enantiomerically pure piperidine derivatives by N-galactosylation of pyridones

European Journal of Organic Chemistry

Volumn , Issue 15, 2004, Pages 3346-3360

  Klegraf, Ellen ^a   Follmann, Markus ^a,b   Schollmeyer, Dieter ^a   Kunz, Horst ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

Author keywords

(5S,9S) Indolizidine 167B; (S) Coniine; Chiral auxiliaries; Conjugate addition; Pyridones

Indexed keywords

1 (BENZYLCARBONYL) 2,3 DIHYDRO 2 PROPYLPYRIDIN 4(1H) ONE; 1 (BENZYLOXYCARBONYL) 2,3 DIHYDRO 2 PROPYLPYRIDIN 4(1H) ONE; 1 (BENZYLOXYCARBONYL) 5 PHENYLSELENYL 2 PROPYLPIPERIDIN 4 ONE; 2 (3 BUTENYL) 2,3 DIHYDRO 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2 [3 [DIMETHYL(PHENYL)SILYL]PROPYL] 3 ETHYL 2,3 DIHYDRO 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2 BUTYL 2,3 DIHYDRO 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2 DECYL 2,3 DIHYDRO 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2 METHYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL) 6 VINYLPIPERIDIN 4 ONE; 2 PROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL) PIPERIDINE; 2 PROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PIPERIDIN 4 ONE; 2,3 DIHYDRO 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL) 2 VINYLPYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2 (3 HYDROXYPROPYL) 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2 (3 METHOXYPHENYL) 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2 [3 [DIMETHYL(PHENYL)SILYL]PROPYL] 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2 ISOPROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2 METHYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2 PHENYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2 PROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4 (1H) ONE; 2,3 DIHYDRO 2 PROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,3 DIHYDRO 3 METHYL 2 PROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PYRIDIN 4(1H) ONE; 2,6 DIPHENYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL) PIPERIDIN 4 ONE; 2,6 DIPROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL) PIPERIDIN 4 ONE; 4 (1,3 DITHIOLAN 2 YL) 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL) 2 PROPYLPIPERIDINE; 5 (PHENYLSELENYL) 2 PROPYL 1 (2,3,4,6 TETRA O PIVALOYL BETA DEXTRO GALACTOPYRANOSYL)PIPERIDIN 4 ONE; CONIINE; DIPYRONE; INDOLIZIDINE ALKALOID; PIPERIDINE DERIVATIVE; PIPERIDONE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ADDITION REACTION; ARTICLE; CHIRALITY; ENANTIOMER; SILYLATION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 4544289291     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400169     Document Type: Article

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