Synthesis of novel C2-symmetric and enantiomerically pure bisbenzoxazoles and bisbenzothiazoles derived from L- and D-tartaric acids

被引：17
作者：
Jiao, P
Xu, JX [1 ]
Zhang, QH
Choi, MCK
Chan, ASC
机构：
[1] Peking Univ, Coll Chem & Mol Engn, Beijing 100871, Peoples R China
[2] Hong Kong Polytech Univ, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2001年 / 12卷 / 22期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1016/S0957-4166(01)00547-X
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Five pairs of novel G-symmetric and enantiomerically pure bisbenzoxazoles and a pair of bisbenzothiazoles derived from L- and D-tartaric acids have been synthesized from L- and D-2,3-O-isopropylidenetartaric dichlorides and o-aminophenol derivatives or o-amino thio phenol, respectively, in two- or one-step reactions. The mechanism for the formation of bisbenzoxazoles and bisbenzothiazoles was suggested. The UV and H-1 NMR spectra showed that no coordination between the bisbenzoheterazoles and Cu(I) or Ni(II) cations occurred due to the lack of a sufficiently basic nitrogen donor atom in the benzoheterazole moiety. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：3081 / 3088
页数：8
相关论文
共 54 条
[1]  
Alexakis A, 2001, SYNLETT, P927
[2]   THE ASYMMETRIC KHARASCH REACTION - CATALYTIC ENANTIOSELECTIVE ALLYLIC ACYLOXYLATION OF OLEFINS WITH CHIRAL COPPER(I) COMPLEXES AND TERT-BUTYL PERBENZOATE [J].
ANDRUS, MB ;
ARGADE, AB ;
CHEN, X ;
PAMMENT, MG .
TETRAHEDRON LETTERS, 1995, 36 (17) :2945-2948
[3]   Catalytic enantioselective allylic oxidation of olefins with copper(I) catalysts and new perester oxidants [J].
Andrus, MB ;
Chen, X .
TETRAHEDRON, 1997, 53 (48) :16229-16240
[4]   Asymmetric allylic oxidation with biarylbisoxazoline-copper(I) catalysis [J].
Andrus, MB ;
Asgari, D .
TETRAHEDRON, 2000, 56 (32) :5775-5780
[5]   Synthesis of macrocyclic polyhydroxy tetralactams derived from L-tartaric acid and beta-hydroxyglutaric acid [J].
Arnaud, N ;
Picard, C ;
Cazaux, L ;
Tisnes, P .
TETRAHEDRON, 1997, 53 (40) :13757-13768
[6]   Investigation of the effects of the structure and chelate size of bis-oxazoline ligands in the asymmetric copper-catalyzed cyclopropanation of olefins: Design of a new class of ligands [J].
Bedekar, AV ;
Koroleva, EB ;
Andersson, PG .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2518-2526
[7]  
Boyd G. V., 1984, COMPREHENSIVE HETERO, V6, P177
[8]   Catalytic asymmetric ring opening of epoxides to chlorohydrins with mild chloride donors and enantiopure titanium complexes [J].
Bruns, S ;
Haufe, G .
TETRAHEDRON-ASYMMETRY, 1999, 10 (08) :1563-1569
[9]   New chiral C-2-symmetric bis(oxazolinylpyridinyl)dioxolane ligands for asymmetric catalysis: palladium catalysed allylic substitution [J].
Chelucci, G .
TETRAHEDRON-ASYMMETRY, 1997, 8 (16) :2667-2670
[10]   Efficient synthetic method for L-tartaramides by aminolysis of reactive 2,3-O-isopropylidene-L-tartaryl chloride [J].
Choi, HJ ;
Kwak, MO ;
Song, H .
SYNTHETIC COMMUNICATIONS, 1997, 27 (07) :1273-1280
123456