Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN
…, H Hausmann, M Kotke, PR Schreiner
Index: Zhang, Zhiguo; Lippert, Katharina M.; Hausmann, Heike; Kotke, Mike; Schreiner, Peter R. Journal of Organic Chemistry, 2011 , vol. 76, # 23 p. 9764 - 9776
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Citation Number: 54
Abstract
We report a new thiourea–Brønsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enantioselectivities 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) ...
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