Chiral Lithium Salts of Phosphoric Acids as Lewis Acid–Base Conjugate Catalysts for the Enantioselective Cyanosilylation of Ketones
- 31 July 2008
- journal article
- research article
- Published by Wiley in Advanced Synthesis & Catalysis
- Vol. 350 (11-12) , 1776-1780
Abstract
The catalytic enantioselective cyanosilylation of aromatic ketones was developed by using chiral lithium salts of (R)‐BINOL‐ or (S)‐BINAM‐derived phosphoric acid compounds. In the presence of 10 mol% of chiral conjugate lithium salts, the corresponding tertiary cyanohydrins were obtained in high yields with moderate to high enantioselectivities. This is the first efficient example of asymmetric catalysis using lithium salts of synthetically useful chiral phosphoric acid compounds. A possible catalytic mechanism and transition states are also discussed as a preliminary working hypothesis.Keywords
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