Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 350, Issue 11-12, Pages 1776-1780Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200800314
Keywords
asymmetric catalysis; cyanohydrins; cyanosilylation; ketones; lithium; phosphoric acids
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Funding
- JSPS
- KAKENHI [20245022]
- MEXT [19750072]
- MEXT
- Toray Science Foundation
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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 1.0 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.
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