Synthesis of Poly(Ethylene Glycol)-Supported (R)-BINOL Derivatives and Their First Application in Enantioselective Mukaiyama Aldol Reactions

被引：8
|
作者：
Zimmer, Reinhold [1 ]
Dekaris, Vjekoslav [1 ]
Knauer, Markus [1 ]
Schefzig, Luise [1 ]
Reissig, Hans-Ulrich [1 ]
机构：
[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany
来源：
SYNTHETIC COMMUNICATIONS | 2009年 / 39卷 / 06期
关键词：
Aldol reaction; asymmetric catalysis; binaphthalene; chiral additives; poly(ethylene glycol); polymer-supported reaction; thioester; CATALYTIC ASYMMETRIC ALLYLATION; CARBONYL-ENE; TITANIUM CATALYST; LEWIS-ACID; BINOL; LIGANDS; DIETHYLZINC; COMPLEXES; ALDEHYDES; MICHAEL;
D O I：
10.1080/00397910802455080
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Mukaiyama aldol reaction of 2-styryl-oxazole-4-carbaldehyde (1) as model substrate with S-ketene silyl acetal 2 catalyzed by poly(ethylene glycol)-supported binaphthyl-derived chiral titanium(IV) complexes afforded the corresponding aldol product in good to excellent yields and enantioselectivities up to 94% ee. The chemical yields and/or the enantioselectivities are enhanced by generating the active catalyst from Ti(OiPr)4, polymer-supported ligands (R)-6 or (R)-8, and chiral or achiral promoters. Pyrrolidine derivative (S)-13 and trifluoromethyl-substituted phenol 12 are the most efficient additives found.
引用
收藏
页码：1012 / 1026
页数：15
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