Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2010(2): 0227-0227
DOI: 10.1055/s-0029-1219136
DOI: 10.1055/s-0029-1219136
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Enantioselective N-Heterocyclic Carbene Catalyzed Mannich Reaction
Y. Kawanaka, E. M. Phillips, K. A. Scheidt*
Northwestern University, Evanston, USA
Further Information
Publication History
Publication Date:
21 January 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201002/lookinside/thumbnails/10.1055-s-0029-1219136-1.jpg)
Significance
An enantioselective addition of α-aryloxyacetaldehyde 3 to aromatic imines 2 was reported to proceed under N-heterocyclic carbene catalysis. Initial products, amino esters E were transformed to the corresponding amides by treatment of the reaction mixture with benzylamine. With chiral precatalyst 1, β-amino amides 4 have been obtained in useful yields and high enantioselectivity. Other in situ transformations of E were also demonstrated affording β-amino alcohols, esters, carboxylic acids or peptides in a one-pot reaction.