A diastereoselective synthesis of 2,4-disubstituted piperidines: Scaffolds for drug discovery

被引:331
作者
Watson, PS [1 ]
Jiang, B [1 ]
Scott, B [1 ]
机构
[1] Dupont Merck Pharmaceut Co, Wilmington, DE 19880 USA
关键词
D O I
10.1021/ol006589o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] A method for the diastereoselective synthesis of 2,4-disubstituted piperidines has been developed which enables the complete control of reaction selectivity merely by changing the order of the reaction sequence. These targets provide convenient platforms for drug discovery which contain easily modified points of diversity.
引用
收藏
页码:3679 / 3681
页数:3
相关论文
共 12 条
[1]   ASYMMETRIC-SYNTHESIS OF 2-ALKYL(ARYL)-2,3-DIHYDRO-4-PYRIDONES BY ADDITION OF GRIGNARD-REAGENTS TO CHIRAL 1-ACYL-4-METHOXYPYRIDINIUM SALTS [J].
COMINS, DL ;
GOEHRING, RR ;
JOSEPH, SP ;
OCONNOR, S .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2574-2576
[2]  
COMINS DL, 1986, TETRAHEDRON LETT, V27, P4549
[3]   PYRIDINE-DERIVED TRIFLATING REAGENTS - AN IMPROVED PREPARATION OF VINYL TRIFLATES FROM METALLO ENOLATES [J].
COMINS, DL ;
DEHGHANI, A .
TETRAHEDRON LETTERS, 1992, 33 (42) :6299-6302
[4]   REGIOSELECTIVE SYNTHESIS OF 4-ALKYL, 5-ALKYL, AND 6-ALKYL AND DIALKYL 5,6-DEHYDROISOQUINUCLIDINES FROM PHENYLVINYLSULFONE CYCLOADDUCTS OF N-ETHOXYCARBONYL-1,2-DIHYDROPYRIDINES [J].
KROW, GR ;
ALSTON, PV ;
SZCZEPANSKI, SW ;
RAGHAVACHARI, R ;
CANNON, KC ;
CAREY, JT .
SYNTHETIC COMMUNICATIONS, 1990, 20 (13) :1949-1958
[5]   MAGNETIC ANISOTROPY OF AMIDE GROUP [J].
PAULSEN, H ;
TODT, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1966, 5 (10) :899-&
[6]   STEREOSPECIFIC TOTAL SYNTHESES OF DECAHYDROQUINOLINE ALKALOIDS (+/-)-195A AND (+/-)-2-EPI-195A [J].
POLNIASZEK, RP ;
DILLARD, LW .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15) :4103-4110
[7]   Ruthenium-catalyzed ring closing olefin metathesis of non-natural alpha-amino acids [J].
Rutjes, FPJT ;
Schoemaker, HE .
TETRAHEDRON LETTERS, 1997, 38 (04) :677-680
[8]   Risperidone compared with new and reference antipsychotic drugs: In vitro and in vivo receptor binding [J].
Schotte, A ;
Janssen, PFM ;
Gommeren, W ;
Luyten, WHML ;
VanGompel, P ;
Lesage, AS ;
DeLoore, K ;
Leysen, JE .
PSYCHOPHARMACOLOGY, 1996, 124 (1-2) :57-73
[9]  
Targum S., 1995, EUR NEUROPSYCHOPHARM, V5, P4
[10]  
WALDMANN H, 1992, J ORG CHEM, V57, P444