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Highly Enantioselective O-H Bond Insertion Reaction of α-Alkyl- and α-Alkenyl-α-diazoacetates with Water

You Li, Yu-Tao Zhao, Ting Zhou, Meng-Qing Chen, Yi-Pan Li, Ming-Yao Huang, Zhen-Chuang Xu, Shou-Fei Zhu* and Qi-Lin Zhou

*The State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China, Email: sfzhunankai.edu.cn

Y. Li, Y.-T. Zhao, T. Zhou, M.-Q. Chen, Y.-P. Li, M.-Y. Huang, Z.-C. Xu, S.-F. Zhu, Q.L. Zhou, J. Am. Chem. Soc., 2020, 142, 10557-10566.

DOI: 10.1021/jacs.0c04532 (free Supporting Information)


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Abstract

The combination of achiral dirhodium complexes and chiral phosphoric acids or chiral phosphoramides enables highly enantioselective O-H bond insertion reactions between water and α-alkyl- and α-alkenyl-α-diazoesters as carbene precursors. This protocol represents an efficient new method for preparation of multifunctionalized chiral α-alkyl and α-alkenyl hydroxyl esters.

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Key Words

α-hydroxy esters


ID: J48-Y2020