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 2008(11): 1218-1218
DOI: 10.1055/s-0028-1083388
DOI: 10.1055/s-0028-1083388
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Gold-Free Aldol-Type Additions of α-Isothiocyanato Imides to Aldehydes
L. Li, E. G. Klauber, D. Seidel*
Rutgers, The State University of New Jersey, Piscataway, USA
Further Information
Publication History
Publication Date:
23 October 2008 (online)

Significance
Seidel and co-workers report an organocatalytic diastereo- and enantioselective aldol addition of α-isothiocyanato imides to aldehydes. The reaction is catalyzed by bifunctional thiourea catalyst 1. A sterically demanding substitution on the imide is necessary for high diastereoselectivities and moreover for suppressing the formation of undesired product 2. The applicability was shown by preparing the protected β-hydroxy-α-amino acid 3 on a large scale and reducing the catalyst loading to 1 mol%.