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Synfacts 2010(7): 0830-0830  
DOI: 10.1055/s-0029-1220114
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

New Backbones for Brønsted Acid Catalysts

Contributor(s): Benjamin List, Olga Lifchits
E. G. Gutierrez, E. J. Moorhead, E. H. Smith, V. Lin, L. K. G. Ackerman, ;C. E. Knezevic, V. Sun, S. Grant, A. G. Wenzel*
Claremont McKenna, Pitzer and Scripps Colleges, USA
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Publication History

Publication Date:
22 June 2010 (online)

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Significance

Wenzel and colleagues report the synthesis of enantiopure phosphoric acid 1 and phosphoramidothioate 2 as novel Brønsted acid catalysts. Taking the key features of the established BINOL-derived analogues 3, the authors designed catalysts 1 and 2 with bulky 3,3′-substituents and electron-withdrawing groups to enhance their acidity. Efficient enantiomer resolution of 1 was performed by crystallization of its cinchonidine salt, while 2 was made from the commercially available (R)-diol. A preliminary investigation of their catalytic efficiency revealed modest results which were nevertheless competitive with those obtained with the established catalysts.