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Highly Enantioselective Friedel-Crafts Reaction of Aromatic Amines with Ethyl Glyoxylate Catalyzed by Chiral Titanium(IV) Complexes: Practical Synthesis of Aminomandelic Acid Derivatives

Yu Yuan, Xingwang Wang, Xin Li, and Kuiling Ding*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. China, Email:

Y. Yuan, X. Wang, X. Li, K. Ding, J. Org. Chem., 2004, 69, 146-149.

DOI: 10.1021/jo034992d


The asymmetric Friedel-Crafts reaction of N,N-dialkylanilines with ethyl glyoxylate has been achieved by the catalysis of titanium complexes of BINOL derivatives to give the corresponding mandelic acid ethyl esters in high yields and good to excellent enantioselectivity.

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Key Words

Friedel-Crafts Reaction, Arylation, α-hydroxy esters

ID: J42-Y2004-200