Synfacts 2009(6): 0682-0682  
DOI: 10.1055/s-0029-1216776
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective Allenoate Additions to Imines

Contributor(s): Benjamin List, Lars Ratjen
B. J. Cowen, L. B. Saunders, S. J. Miller*
Yale University, New Haven, USA
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25. Mai 2009 (online)


A peptide-catalyzed enantioselective allenoate addition to N-acyl imines is reported. Among different examined catalysts, all capable to adopt β-turn conformations, a peptide which is composed of a phenylalanine, an amino-isobutyric acid, a proline and a pyridylalanine (Pal) moiety proved to be the most beneficial species. Variously substituted aromatic and aliphatic im­ines react with allenoates furnishing the products in satisfactory yields and good enantioselectivities.