Leipeng Xue, Jiahui Li, Tianxu Yu, Lei He, Jiaqi Hou, Qihang Cai, Chao Yao, Yue-Ming Li
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引用次数: 0
Abstract
Here, we demonstrated a copper(II)-catalyzed enantioselective addition of aryl amines to isatin-derived N-Boc-ketimines using chiral O–N–N tridentate ligands derived from BINOL and proline. Generally, the chiral acyclic N,N′-ketals were obtained in high yields (up to 98%) and excellent ee values (up to 98%). Various aryl amines could be tolerated and a gram-scale reaction was also possible. Further, an X-ray diffraction experiment confirmed that the configuration of isatin-derived N-Boc ketimine should be (Z). Confirmation of the configuration of the ketimine would make it easier to understand the rationale for stereofacial selective activation of the electrophile with either organo- or Lewis acid–based catalysts.
期刊介绍:
Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.