Asymmetric Friedel-Crafts reactions of vinyl ethers with fluoral catalyzed by chiral binaphthol-derived titanium catalysts

被引：32

作者：

Ishii, A ^{[1
]}

Mikami, K ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Chem Technol, Meguro Ku, Tokyo 1528552, Japan

来源：

JOURNAL OF FLUORINE CHEMISTRY | 1999年 / 97卷 / 1-2期

关键词：

Friedel-Crafts reaction; asymmetric catalysis; fluoral; vinyl ether;

D O I：

10.1016/S0022-1139(99)00025-1

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Asymmetric Friedel-Crafts reactions of vinyl ethers with fluoral catalyzed by chiral binaphthol-derived titanium catalysts gave reactive vinyl ether products. Sequential diastereoselective reactions of resultant vinyl ethers with m-CPBA provided highly functionalized organofluorine compounds in high enantiomeric purity. (C) 1999 Elsevier Science S.A. All rights reserved.

引用

页码：51 / 55

页数：5

共 28 条

[1] SYNTHESIS OF OPTICALLY-ACTIVE 4-HYDROXYMANDELIC ACID AND DERIVATIVES VIA REGIOSELECTIVE AND STEREOSELECTIVE FRIEDEL-CRAFTS ALKYLATION
BIGI, F
SARTORI, G
MAGGI, R
CANTARELLI, E
GALAVERNA, G
[J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (12) : 2411 - 2414
[2] ASYMMETRIC ELECTROPHILIC SUBSTITUTION ON PHENOLS .1. ENANTIOSELECTIVE ORTHO-HYDROXYALKYLATION MEDIATED BY CHIRAL ALKOXYALUMINUM CHLORIDES
BIGI, F
CASIRAGHI, G
CASNATI, G
SARTORI, G
FAVA, GG
BELICCHI, MF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (25) : 5018 - 5022
[3] ASYMMETRIC ELECTROPHILIC SUBSTITUTION ON PHENOLS .2. ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF ORTHO-HYDROXYATROLACTIC ESTERS
CASIRAGHI, G
BIGI, F
CASNATI, G
SARTORI, G
SONCINI, P
FAVA, GG
BELICCHI, MF
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) : 1779 - 1785
[4] Asymmetric Friedel-Crafts reaction mediated by new chiral auxiliaries derived from (1S)-(-)-beta-pinene: Enantioselective synthesis of (-)-8-norethyl,1'-normethyl etodolac
Costa, PRR
Cabral, LM
Alencar, KG
Schmidt, LL
Vasconcellos, MLAA
[J]. TETRAHEDRON LETTERS, 1997, 38 (40) : 7021 - 7024
[5] NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS
DALE, JA
MOSHER, HS
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) : 512 - 519
[6] ElKaim L, 1996, TETRAHEDRON LETT, V37, P375
[7] ENANTIOSELECTIVE CATALYSIS WITH A NEW ZIRCONIUM TRICHLORIDE LEWIS ACID CONTAINING A DIBORNACYCLOPENTADIENYL LIGAND
ERKER, G
VANDERZEIJDEN, AAH
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (05): : 512 - 514
[8] Heaney H., 1991, COMPREHENSIVE ORGANI, V2, P733
[9] ACYCLIC STEREOSELECTION .4. ASSIGNMENT OF STEREOSTRUCTURE TO BETA-HYDROXYCARBONYL COMPOUNDS BY C-13 NUCLEAR MAGNETIC-RESONANCE
HEATHCOCK, CH
PIRRUNG, MC
SOHN, JE
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (24) : 4294 - 4299
[10] ALLYLIC 1,3-STRAIN AS A CONTROLLING FACTOR IN STEREOSELECTIVE TRANSFORMATIONS
HOFFMANN, RW
[J]. CHEMICAL REVIEWS, 1989, 89 (08) : 1841 - 1860

← 1 2 3 →