Change search
ReferencesLink to record
Permanent link

Direct link
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
Show others and affiliations
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
Abstract [en]

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.
Keyword [en]
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
National Category
Chemical Sciences
URN: urn:nbn:se:kth:diva-15285DOI: 10.1021/ja056120uISI: 000234258700062OAI: diva2:333326
QC 20100525Available from: 2010-08-05 Created: 2010-08-05 Last updated: 2012-02-28Bibliographically approved

Open Access in DiVA

No full text

Other links

Publisher's full text

Search in DiVA

By author/editor
Franzen, Johan.
In the same journal
Journal of the American Chemical Society
Chemical Sciences

Search outside of DiVA

GoogleGoogle Scholar
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

Altmetric score

Total: 33 hits
ReferencesLink to record
Permanent link

Direct link