Current Organic Chemistry

Author(s): Pinaki S. Bhadury, Yuanyong Yao and Yongguang He

DOI: 10.2174/138527212802651313

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Organocatalytic Application of Axially Dissymmetric BINOLs and their Conversion into Binaphthyl Phosphoric Acids

Page: [1730 - 1753] Pages: 24

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Abstract

3,3’-disubstituted axially dissymmetric BINOLS, owing to their lower acidity have limited organocatalytic applications in stereoselective transformations. Nevertheless, they serve as potent and immediate precursors to much stronger Brønsted acids e.g. binaphthyl phosphoric acids. The review lists some suitably substituted and sterically demanding BINOLS, their use in organic transformations and possibility to convert them into stronger Bronsted acids as more effective organocatalysts.

Keywords: Asymmetric Organocatalysis, Dissymmetric BINOL, Chiral Phosphoric Acids, Hydrogen-Bond, Synthesis, stereoselective, nucleophile, electrophile, 1, 1’-binaphthyl-2, 2’-diols, enantioselective, allylboration