Highly Atroposelective Synthesis of Arylpyrroles by Catalytic Asymmetric Paal–Knorr Reaction

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• 作者：Lei Zhang ; Jian Zhang ; Ji Ma ; Dao-Juan Cheng ; Bin Tan
• 刊名：Journal of the American Chemical Society
• 出版年：2017
• 出版时间：February 8, 2017
• 年：2017
• 卷：139
• 期：5
• 页码：1714-1717
• 全文大小：457K
• ISSN：1520-5126

文摘

A general and efficient method for accessing enantiomerically pure arylpyrroles by utilizing the catalytic asymmetric Paal-Knorr reaction has been developed for the first time. A wide range of axially chiral arylpyrroles were obtained in high yields with good to excellent enantioselectivities. The key to success is the use of the combined-acid catalytic system involving a Lewis acid and a chiral phosphoric acid for achieving effective enantiocontrol. Noteworthy is that an unexpected solvent-dependent inversion of the enantioselectivity was observed in the above-mentioned asymmetric reaction.