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Synfacts 2010(10): 1189-1189  
DOI: 10.1055/s-0030-1258673
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Precipitation Induced Nonlinear Effects in Phosphoric Acid Catalysis

Contributor(s): Benjamin List, Ji-Woong Lee
N. Li, X.-H. Chen, S.-M. Zhou, S.-W. Luo, J. Song, L. Ren, L.-Z. Gong*
University of Science and Technology of China, Hefei, Chengdu Institute of Organic Chemistry and Graduate School of Chinese Academy of Sciences, Beijing, P. R. of China
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Publication History

Publication Date:
22 September 2010 (online)

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Significance

A strong positive nonlinear effect (NLE) of phosphoric acid catalyst 1 is reported (see also: D. G. Blackmond and co-workers ­Nature 2006, 441, 621). The single crystal structures of racemic and enantiopure 1 have different patterns of hydrogen bonding networks with water, which render an energy difference between a racemate and a conglomerate. Also, a positive NLE was observed for various reactions with substrates, which do not contain a hydrogen bonding interrupting functional group. Otherwise, a NLE could not be observed with basic substrates, which can disturb hydrogen bonding and dissolve the catalyst in a non-polar solution. However, after removing precipitated phosphate 1, a NLE could be detected for the reactions with basic substrates.