Highly Enantio- and Diastereoselective [4 + 2] Cycloaddition of 5H-oxazol-4-ones with N-Maleimides

详细信息    查看全文

• 作者：Shuai Qiu ; Richmond Lee ; Bo Zhu ; Michelle L. Coote ; Xiaowei Zhao ; Zhiyong Jiang
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：September 2, 2016
• 年：2016
• 卷：81
• 期：17
• 页码：8061-8069
• 全文大小：491K
• 年卷期：0
• ISSN：1520-6904

文摘

An organocatalytic asymmetric reaction between 5H-oxazol-4-ones and N-substituted maleimides is disclosed. Employing Takemoto’s chiral tertiary amine–thiourea as the catalyst, [4 + 2] annulation reactions were performed with high chemoselectivity, leading to a series of biologically important chiral oxo-bridged piperidone-fused succinimides in good to excellent enantioselectivities (up to >99% ee) and >19:1 dr.