SYNTHESIS OF OPTICALLY-ACTIVE 4-HYDROXYMANDELIC ACID AND DERIVATIVES VIA REGIOSELECTIVE AND STEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION

被引：16

作者：

BIGI, F

SARTORI, G

MAGGI, R

CANTARELLI, E

GALAVERNA, G

机构：

[1] Dipartimento di Chimica Organica, Industriale dell'Università, I-43100 Parma, Viale delle Scienze

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 12期

关键词：

D O I：

10.1016/S0957-4166(00)82212-0

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Optically active 4-hydroxymandelic esters were prepared in good yields and very high diastereoselectivity (up to 96% d.e.) via para-hydroxyalkylation of phenolic ethers. Enantiomeric pure 4-hydroxymandelic acid is available by hydrolysis.

引用

页码：2411 / 2414

页数：4

共 20 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 - SYNTHESIS OF 2-HYDROXYMANDELIC ESTERS [J].

BIGI, F ;

CASNATI, G ;

SARTORI, G ;

DALPRATO, C ;

BORTOLINI, R .

TETRAHEDRON-ASYMMETRY, 1990, 1 (12) :861-864

[3]

BOUZARD D, 1977, Patent No. 1494890

[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] TEMPLATE CATALYSIS VIA NON-TRANSITION METAL-COMPLEXES - NEW HIGHLY SELECTIVE SYNTHESES ON PHENOL SYSTEMS [J].

CASNATI, G ;

CASIRAGHI, G ;

POCHINI, A ;

SARTORI, G ;

UNGARO, R .

PURE AND APPLIED CHEMISTRY, 1983, 55 (11) :1677-1688

[6] SELECTIVE DEPROTECTION OF ALCOHOLIC AND PHENOLIC SILYL ETHERS [J].

COLLINGTON, EW ;

FINCH, H ;

SMITH, IJ .

TETRAHEDRON LETTERS, 1985, 26 (05) :681-684

[7]

EDWARDS PN, 1983, Patent No. 634825

[8] STUDIES DIRECTED TOWARD SYNTHESIS OF PROSTAGLANDINS - USEFUL BORON-MEDIATED OLEFIN SYNTHESES [J].

EVANS, DA ;

CRAWFORD, TC ;

THOMAS, RC ;

WALKER, JA .

JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (25) :3947-3953

[9]

GALAVERNA G, IN PRESS J CHROMATOG

[10]

HONDA Y, 1989, Patent No. 1221345

← 1 2 →