Enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine.

被引:27
作者
Lygo, B
Crosby, J
Lowdon, TR
Wainwright, PG
机构
[1] ZENECA PHARMACEUT,MACCLESFIELD SK10 2NA,CHESHIRE,ENGLAND
[2] HICKSON & WELCH LTD,CASTLEFORD WF10 2JT,W YORKSHIRE,ENGLAND
关键词
D O I
10.1016/S0040-4039(97)00310-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An enantio- and diastereoselective synthesis of all four possible stereoisomers of 2-(phenylhydroxymethyl)quinuclidine is reported. Key steps involve the use of the Sharpless dihydroxylation protocol to induce asymmetry, and stereodivergent cyclisations of the resulting diol to form the quinuclidine ring. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2343 / 2346
页数:4
相关论文
共 16 条
[1]   STEREOSPECIFIC SYNTHESIS OF A QUINUCLIDINYL ANALOG OF MEFLOQUINE .4. [J].
ADAM, S .
TETRAHEDRON, 1994, 50 (11) :3327-3332
[2]   SYNTHESIS OF THE SELECTIVE MUSCARINIC AGONIST (3R)-3-(6-CHLOROPYRAZIN-2-YL)-1-AZABICYCLO[2.2.2]OCTANE [J].
ASHWOOD, MS ;
GIBSON, AW ;
HOUGHTON, PG ;
HUMPHREY, GR ;
ROBERTS, DC ;
WRIGHT, SHB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (06) :641-644
[3]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[4]   SOLVOLYSE VON 2-(ALPHA-CHLORBENZYL)-CHINUCLIDIN ZUR KENNTNIS DER HETEROCINCHONIN-UMLAGERUNG [J].
BRASCHLER, V ;
KAISER, A ;
GROB, CA .
HELVETICA CHIMICA ACTA, 1963, 46 (07) :2646-&
[5]   TOTAL SYNTHESIS OF CINCHONA ALKALOIDS .2. STEREOSELECTIVE TOTAL SYNTHESES OF QUININE AND QUINIDINE [J].
GUTZWILLER, J ;
USKOKOVIC, MR .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1978, 100 (02) :576-581
[6]   A SIMPLIFIED PROCEDURE FOR THE STEREOSPECIFIC TRANSFORMATION OF 1,2-DIOLS INTO EPOXIDES [J].
KOLB, HC ;
SHARPLESS, KB .
TETRAHEDRON, 1992, 48 (48) :10515-10530
[7]   TOWARD AN UNDERSTANDING OF THE HIGH ENANTIOSELECTIVITY IN THE OSMIUM-CATALYZED ASYMMETRIC DIHYDROXYLATION (AD) .1. KINETICS [J].
KOLB, HC ;
ANDERSSON, PG ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (04) :1278-1291
[8]  
Noyori R., 1994, ASYMMETRIC CATALYSIS
[9]  
ODonnell M. J., 1993, CATALYTIC ASYMMETRIC, P389
[10]  
PLUIM H, 1982, THESIS RIJKSUNIVERSI