Synthesis of several polyethers derived from BINOL and their application in the asymmetric borane reduction of prochiral ketones

被引：15
作者：
Zhang, An-Lin [1 ]
Yu, Zeng-da [1 ]
Yang, Li-Wen [1 ]
Yang, Nian-Fa [1 ]
机构：
[1] Xiangtan Univ, Coll Chem, Key Lab Environm Friendly Chem & Applicat, Minist Educ, Xiangtan 411105, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2015年 / 26卷 / 04期
基金：
美国国家科学基金会;
关键词：
POLYMER-SUPPORTED CATALYSTS; TRANSITION-METAL-COMPLEXES; DIELS-ALDER REACTIONS; ENANTIOSELECTIVE ADDITION; OXAZABOROLIDINE CATALYST; FLUORESCENT SENSOR; HELICAL POLYMERS; TITANIUM COMPLEX; CHIRAL LIGANDS; ALDEHYDES;
D O I：
10.1016/j.tetasy.2014.12.012
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Several novel epoxy monomers, (S,S)- or (S,R)-3-(glycidyloxy)methy1-2,2'-bis(methoxymethyloxy)-1, 1'-binaphthalene and (S,S)- or (S,R)-6-(glycidyloxy)methy1-2,2'-bis(methoxymethyloxy)-1,1'-binaphthalene, which were derived from chiral BINOL and epichlorohydrin, were synthesized and underwent anionic polymerization and deprotection of the MOM groups to obtain soluble polyethers. These polyethers were used to induce the enantioselective borane reduction of prochiral ketones. The substrates gave up to 98% yield with over 99% ee values. The recovered polyethers could be reused many times to induce the enantioselective reduction of prochiral ketones without losing their enantioselective induction ability. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：173 / 179
页数：7
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