Enantioselective addition of phenylacetylene to aldehydes catalyzed by a D-glucosamine-derived sulfonamide-titanium complex

被引：10
|
作者：
Bauer, Tomasz [1 ]
Smolinski, Slawomir [1 ]
Gawel, Przemyslaw [1 ]
Jurczak, Janusz [1 ,2 ]
机构：
[1] Warsaw Univ, Dept Chem, PL-02093 Warsaw, Poland
[2] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 38期
关键词：
D-Glucosamine; Aldehydes; Phenylacetylene; Enantioselective; CARBONYL GROUPS; AMIDE) LIGANDS; ALKYNYLATION; ALKYNYLZINC; DERIVATIVES; DIETHYLZINC; KETONES;
D O I：
10.1016/j.tetlet.2011.07.051
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We present the synthesis of beta-hydroxy sulfonamides derived from D-glucosamine and their application as ligands in titanium tetraisopropoxide promoted enantioselective addition of phenylacetylene to benzaldehyde and selected aromatic and aliphatic aldehydes. The N-3,5-bis(trifluoromethyl)benzenesulfonamido-D-glucosamine derivative was chosen as the most efficient ligand for this addition. The reaction is highly enantioselective for several aromatic aldehydes and enantiomeric excesses up to 92% were obtained. (C) 2011 Elsevier Ltd. All rights reserved.
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收藏
页码：4882 / 4884
页数：3
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