By Daniela Kampen, Corinna M. Reisinger, Benjamin List (auth.), Benjamin List (eds.)
Kerstin Etzenbach-Effers, Albrecht Berkessel: Non-Covalent Organocatalysis in line with Hydrogen Bonding: Elucidation of response Paths through Computational Methods.- Petri M. Pihko, Inkeri Majander, and Anniina Erkkilä: Enamine Catalysis.- Jennifer L. Moore, Tomislav Rovis: Lewis Base Catalysts 6: Carbene Catalysts.- Amal Ting, Jennifer M. Goss, Nolan T. McDougal, and Scott E. Schaus: Brønsted Base Catalysts.- O. Andrea Wong, Yian Shi: Chiral Ketone and Iminium Catalysts for Olefin Epoxidation.- Alan C. Spivey, Stellios Arseniyadis: Amine, Alcohol and Phosphine Catalysts for Acyl move Reactions.- John B. Brazier, Nicholas C.O. Tomkinson: Lewis Base Catalysts 2 Secondary and first Amine Catalysts for Iminium Catalysis.- Oksana Sereda, Sobia Tabassum, and René Wilhelm: Lewis Acid Organocatalysts.- Daniela Kampen , Corinna M. Reisinger , and Benjamin checklist: Chiral Bronsted Acids for C Organocatalysis.-
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Extra info for Asymmetric Organocatalysis
The reaction proceeds via a concerted but asynchronous pathway, and no zwitterionic intermediate or transition state corresponding to a stepwise Mukaiyama-aldol type pathway could be located. The partial charges of the aldehyde carbonyl group are stabilized by an intermolecular hydrogen bond to the TADDOL catalyst. In the organocatalytic reaction, the C–C bond formation has progressed further (due to the more positively polarized carbonyl carbon atom of the benzaldehyde) whereas the C–C bond formation lags behind in the uncatalyzed reaction.
Svensson M, Humbel S, Froese RDJ, Matsubara T, Sieber S, Morokuma KJ (1996) J Phys Chem 100:19357 61. Stewart JJP (1989) J Comput Chem 10:209 62. Stewart JJP (1989) J Comput Chem 10:221 63. Du H, Zhao D, Ding K (2004) Chem Eur J 10:5964 64. 1007/128_2008_21 © Springer-Verlag Berlin Heidelberg 2009 Published online: 21 May 2009 Enamine Catalysis Petri M. Pihko, Inkeri Majander, and Anniina Erkkilä Abstract The reversible reaction of primary or secondary amines with enolizable aldehydes or ketones affords nucleophilic intermediates, enamines.
1 Aldol and Related Reactions Among the electrophilic reaction partners of the enamine nucleophiles, aldehydes and ketones are arguably the most important class. The addition of an enamine to a carbonyl compound affords aldol products after hydrolysis (Scheme 13). In this process, one or two new stereogenic centers and one carbon-carbon bond are formed. 42 P. M. Pihko et al. O R R3 N R R4 ±H R4 R1 R1 R2 R2 enamine O + H2O OH N R3 − R R4 R2 N H2 iminium intermediate OH R1 R3 aldol product Scheme 13 Enamine-catalyzed aldol reaction Usually, the component that forms the enamine is called aldol donor, and the electrophilic carbonyl component is called acceptor (Scheme 14).
Asymmetric Organocatalysis by Daniela Kampen, Corinna M. Reisinger, Benjamin List (auth.), Benjamin List (eds.)