Direct Catalytic Asymmetric Conjugate Addition of Saturated and Unsaturated Thioamides

详细信息    查看全文

• 作者：Nilanjana Majumdar ; Akira Saito ; Liang Yin ; Naoya Kumagai ; Masakatsu Shibasaki
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：July 2, 2015
• 年：2015
• 卷：17
• 期：13
• 页码：3362-3365
• 全文大小：391K
• ISSN：1523-7052

文摘

Direct catalytic asymmetric conjugate addition of thiolactams to 伪,尾-unsaturated thioamides was efficiently promoted by a soft Lewis acid/hard Br酶nsted base cooperative catalyst in a highly stereocontrolled manner. Thioamide functionality was crucial to promote both the efficient enolization of thiolactam pronucleophiles and the subsequent stereoselective conjugate addition to 伪,尾-unsaturated thioamides. Differential manipulation of the two thioamide functionalities of the product highlights the synthetic utility of the present catalytic system.