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J Am Chem Soc. 2013 Nov 13;135(45):16849-52. doi: 10.1021/ja409859x. Epub 2013 Oct 30.

A highly efficient and enantioselective intramolecular Cannizzaro reaction under TOX/Cu(II) catalysis.

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State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, P.R. China.


An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.


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