A general organocatalyst for direct alpha-functionalization of aldehydes: Stereoselective C-C, C-N, C-F, C-BR, and C-S bond-forming reactions. Scope and mechanistic insights
2005 (English)In: Journal of the American Chemical Society, ISSN 0002-7863, E-ISSN 1520-5126, Vol. 127, no 51, 18296-18304 p.Article in journal (Refereed) Published
The development of a general organocatalyst for the alpha-functionalization of aldehydes, via an enamine intermediate, is presented. Based on optically active alpha,alpha-diarylprolinol silyl ethers, the scope and applications of this catalyst for the stereogenic formation of C-C, C-N, C-F, C-Br, and C-S bonds are outlined. The reactions all proceed in good to high yields and with excellent enantioselectivities. Furthermore, we will present mechanistic insight into the reaction course applying nonlinear effect studies, kinetic resolution, and computational investigations leading to an understanding of the properties of the alpha,alpha-diarylprolinol silyl ether catalysts.
Place, publisher, year, edition, pages
2005. Vol. 127, no 51, 18296-18304 p.
asymmetric aldol reactions, amino-acid-derivatives, mannich-type reactions, enantioselective synthesis, michael reactions, alpha, alpha-disubstituted aldehydes, alpha, beta-unsaturated aldehydes, 1, 2-amino alcohols, enamine catalysis, l-prolinamide
IdentifiersURN: urn:nbn:se:kth:diva-15285DOI: 10.1021/ja056120uISI: 000234258700062OAI: oai:DiVA.org:kth-15285DiVA: diva2:333326
QC 201005252010-08-052010-08-052012-02-28Bibliographically approved