Cyclodextrin host as a supramolecular catalyst in nonpolar solvents: stereoselective synthesis of (E)-3-alkylideneoxindoles

被引：22
作者：
Asahara, Haruyasu [1 ]
Kida, Toshiyuki [1 ]
Hinoue, Tomoaki [1 ]
Akashi, Mitsuru [1 ]
机构：
[1] Osaka Univ, Dept Appl Chem, Grad Sch Engn, Suita, Osaka 5650871, Japan
来源：
TETRAHEDRON | 2013年 / 69卷 / 45期
关键词：
Cyclodextrin; Oxindole; Inclusion complex; Stereoselective reaction; 3-SUBSTITUTED INDOLIN-2-ONES; ENANTIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; CONSTRUCTION; OXINDOLES; RECEPTOR; BINDING; RECOGNITION; CYCLIZATION; STRATEGIES;
D O I：
10.1016/j.tet.2013.08.078
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Heptakis(6-O-triisopropylsilyl)-beta-cyclodextrin (TIPS-beta-CD) effectively formed inclusion complexes with oxindole and its derivatives as guests in nonpolar solvents. Their inclusion complex formation was remarkably affected by the position and size of substituents on the oxindole ring of the guest. The Knoevenagel condensation reaction of these oxindoles with cinnamaldehyde to give 3-alkylideneoxindoles was accelerated with enhanced E/Z selectivities in the presence of catalytic amounts of TIPS-beta-CD. (C) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9428 / 9433
页数：6
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