HIGHLY REGIOSELECTIVE AND DIASTEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION OF PHENOLS - SYNTHESIS OF 2-HYDROXYMANDELIC ESTERS

被引:31
作者
BIGI, F
CASNATI, G
SARTORI, G
DALPRATO, C
BORTOLINI, R
机构
[1] Istituto di Chimica Organica dell'Università, I-43100 Parma, Viale delle Scienze
关键词
D O I
10.1016/S0957-4166(00)82274-0
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Ortho-hydroxyalkylaton of phenol substrates was performed via coordinative complexes of metal phenolates with chiral glyoxylates: optically active 2-hydroxymandelic esters have been obtained with good yields and very high diastereoselectivity (up to 94% d.e.).
引用
收藏
页码:861 / 864
页数:4
相关论文
共 17 条
[1]   NOVEL SPONGE-DERIVED AMINO-ACIDS .11. THE ENTIRE ABSOLUTE STEREOCHEMISTRY OF THE BENGAMIDES [J].
ADAMCZESKI, M ;
QUINOA, E ;
CREWS, P .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :240-242
[2]   HIGHLY REGIOSELECTIVE AND DIASTEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION OF PHENOLS WITH ALPHA-AMINO ALDEHYDES - SYNTHESIS OF OPTICALLY-ACTIVE EPHEDRINE-LIKE COMPOUNDS [J].
BIGI, F ;
CASNATI, G ;
SARTORI, G ;
ARALDI, G ;
BOCELLI, G .
TETRAHEDRON LETTERS, 1989, 30 (09) :1121-1124
[3]   ASYMMETRIC ELECTROPHILIC SUBSTITUTION ON PHENOLS .1. ENANTIOSELECTIVE ORTHO-HYDROXYALKYLATION MEDIATED BY CHIRAL ALKOXYALUMINUM CHLORIDES [J].
BIGI, F ;
CASIRAGHI, G ;
CASNATI, G ;
SARTORI, G ;
FAVA, GG ;
BELICCHI, MF .
JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) :5018-5022
[4]   SELECTIVE REACTIONS USING METAL PHENOXIDES .1. REACTIONS WITH FORMALDEHYDE [J].
CASIRAGHI, G ;
CASNATI, G ;
CORNIA, M ;
POCHINI, A ;
PUGLIA, G ;
SARTORI, G ;
UNGARO, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (04) :318-321
[5]   ASYMMETRIC ELECTROPHILIC SUBSTITUTION ON PHENOLS .2. ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF ORTHO-HYDROXYATROLACTIC ESTERS [J].
CASIRAGHI, G ;
BIGI, F ;
CASNATI, G ;
SARTORI, G ;
SONCINI, P ;
FAVA, GG ;
BELICCHI, MF .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1779-1785
[6]   STEREOSELECTIVE ORGANIC-REACTIONS - CATALYSTS FOR CARBONYL ADDITION PROCESSES [J].
EVANS, DA .
SCIENCE, 1988, 240 (4851) :420-426
[7]  
HOEFNAGEL AJ, 1988, RECL TRAV CHIM PAY B, V107, P242
[8]  
HOREAU A, 1968, B SOC CHIM FR, P3795
[9]  
MORRISON JD, 1983, ASYMMETRIC SYNTHESIS
[10]   ENANTIOSELECTIVE SYNTHESIS OF OPTICALLY PURE S-ISOSERINE [J].
SOLLADIECAVALLO, A ;
KHIAR, N .
TETRAHEDRON LETTERS, 1988, 29 (18) :2189-2192