Chiral Sodium Phosphate Catalyzed Enantioselective 1,4-Addition of TMSCN to Aromatic Enones

被引：40

作者：

Yang, Jingya ^{[1
,2
]}

Wu, Shaoxiang ^{[1
]}

Chen, Fu-Xue ^{[1
]}

机构：

[1] Beijing Inst Technol, Sch Chem Engn & Environm, Dept Appl Chem, Beijing 100081, Peoples R China

[2] NW Normal Univ, Coll Chem & Chem Engn, Lanzhou 730070, Peoples R China

来源：

SYNLETT | 2010年 / 18期

关键词：

asymmetric catalysis; enones; 1,4-addition; nitriles; phosphates; ASYMMETRIC MICHAEL ADDITION; MANNICH-TYPE REACTION; CONJUGATE ADDITION; ALPHA; BETA-UNSATURATED IMIDES; LITHIUM BINAPHTHOLATE; GRIGNARD-REAGENTS; PHOSPHORIC-ACIDS; RECENT PROGRESS; ALDOL REACTION; CYANIDE;

D O I：

10.1055/s-0030-1258817

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile enantioselective 1,4-addition of TMSCN to aromatic enones has been developed using chiral sodium phosphate. Thus, in the presence of 20 mol% of sodium salt generated in situ from (R)-3,3'-di(1-adamantyl)-1,1'-binaphthyl-2,2'-diylphosphoric acid and NaOH, beta-cyano ketones were obtained in high yield (86-96%) and up to 72% ee within three hours at 80 degrees C in toluene.

引用

页码：2725 / 2728

页数：4

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