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Hydrogen-Bonding Directed Reversal of Enantioselectivity

Wei Zeng, Guo-Ying Chen, Yong-Gui Zhou* and Yu-Xue Li

*Dalian Institute of Chemical Physics, CAS, 457 Zhongshan Lu, Dalian 116023, China, Email:

W. Zeng, G.-Y. Chen, Y.-G. Zhou, Y.-X. Li, J. Am. Chem. Soc., 2007, 129, 750-751.

DOI: 10.1021/ja067346f

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A successful stereochemical reversal in AgOAc catalyzed [3+2] cycloaddition is based on the formation of hydrogen bonding between ligand and reactant. Simple ligand design provides an efficient and convenient route to prepare both enantiomers of a chiral compound.

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Key Words

1,3-dipolar cycloadditions, pyrrolidines

ID: J48-Y2007-0190