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Diastereomeric Aziridine Carbinol Catalyzed Enantioselective Arylation Reaction: Toward the Asymmetric Synthesis of Both Enantiomers of Chiral 3-Aryl Phthalide

Xixi Song, Yuan-Zhao Hua, Jing-Guo Shi, Ping-Ping Sun, Min-Can Wang* and Junbiao Chang*

*The College of Chemistry and Molecular Engineering, Zhengzhou University, No. 75 Daxue Road, Zhengzhou, Henan Province 450052, P. R. China, Email: wangmincanzzu.edu.cn, changjunbiaozzu.edu.cn

X. Song, Y.-Z. Hua, J.-G. Shi, P.-P. Sun, M.-C. Wang, J. Chang, J. Org. Chem., 2014, 79, 6087-6093.

DOI: 10.1021/jo500796w (free Supporting Information)


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Abstract

Diastereomeric aziridine carbinols are applied as efficient chiral ligand in a catalyzed asymmetric arylation and sequential arylation-lactonization cascade. The two diastereomers, which are facilely synthesized from the same chiral source, function as pseudo enantiomers in arylation of aromatic aldehydes providing the different enantiomers of the diarylmethanols with almost the same excellent enantioselectivities.

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Key Words

Diarylmethanols


ID: J42-Y2014