Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 76, Issue 23, Pages 9764-9776Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo201864e
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Funding
- Deutsche Forschungsgemeinschaft [SPP 1179]
- Justus-Liebig University (Junior Science and Teaching Units) [60000434]
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We report a new thiourea-Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enamioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.
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