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

Full Text: HTML

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) ...

Related Articles:

Metal or ammonium alginates as Lewis base catalysts for the 1, 2-addition of silyl nucleophiles to carbonyl compounds

[Verrier, Cecile; Oudeyer, Sylvain; Dez, Isabelle; Levacher, Vincent Tetrahedron Letters, 2012 , vol. 53, # 15 p. 1958 - 1960]

Chiral zirconium alkoxides-mediated asymmetric Meerwein-Ponndorf-Verley cyanation of aldehydes

[Ooi, Takashi; Takaya, Keisuke; Miura, Tomoya; Maruoka, Keiji Synlett, 2000 , # 1 p. 69 - 70]

Dibutyltin Dimethoxide??Catalyzed Cyano Transfer to Aldehydes and Imines

[Yanagisawa, Akira; Matsumoto, Takuya; Kushihara, Naoyuki; Yoshida, Kazuhiro Advanced Synthesis and Catalysis, 2010 , vol. 352, # 17 p. 2918 - 2922]

Studies on oxygen heterocycles: Part-1: Acid catalysed and photochemical reactions of some aryldiazoketones

[Ghosh, Somnath; Datta, Indira; Chakraborty, Rupak; Das, Tapas Kumar; Sengupta, Judhajit; Sarkar, Dipak Chandra Tetrahedron, 1989 , vol. 45, # 5 p. 1441 - 1446]

CCCXXXVI.—The conditions determining the thermodynamic stability of cyanohydrins of carbonyl compounds. Part I. Some effects of (a) substitution in aromatic …

[Lapworth; Manske Journal of the Chemical Society, 1928 , p. 2546]

More Articles...