Chiral sulfamide-catalyzed asymmetric Michael addition of protected 3-hydroxypropanal to 尾-nitrostyrenes

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• 作者：Simone Tortoioli^a ; ^{simone.tortoioli@actelion.com} ; Sergio Bacchi^b ; Cecilia Tortoreto^c ; John B. Strachan^d ; Alcide Perboni^b
• 关键词：Asymmetric organocatalysis ; Chiral sulfamides ; Michael addition ; Trans-尾-nitrostyrenes ; C&ndash ; C bond
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：11 April, 2012
• 卷：53
• 期：15
• 页码：1878-1881
• 文件大小：574 K

摘要

Organocatalytic asymmetric Michael addition of 3-(OTBS)-propanal to 尾-nitrostyrenes catalyzed by chiral sulfamides was investigated. Good d.r. (up to 80:20) and excellent enantioselectivities (up to >99%ee) were achieved. Both the N-[(1R,2R)-2-aminocyclohexyl]-N鈥?(phenylmethyl)sulfamide 7b and the novel chiral N-[(1R,2R)-2-aminocyclohexyl]-N鈥?[3,5-bis(trifluoromethyl)phenyl]sulfamide 7a were identified as efficient primary amine organocatalysts.