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A Highly Efficient and Enantioselective Intramolecular Cannizzaro Reaction under TOX/Cu(II) Catalysis

Pan Wang, Wen-Jie Tao, Xiu-Li Sun, Saihu Liao* and Yong Tang*

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, P.R. China, Email: shliaosioc.ac.cn, tangysioc.ac.cn

P. Wang, W.-J. Tao, X.-L. Sun, S. Liao, Y. Tang, J. Am. Chem. Soc., 2013, 135, 16849-16852.

DOI: 10.1021/ja409859x (free Supporting Information)


Abstract

An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols offers an unprecedented high level of enantioselectivity in the presence of a congested TOX ligand and if active glyoxals are gradually liberated from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity.

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Key Words

Cannizzaro reaction, Mandelic Acid Derivatives


ID: J48-Y2013