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Synfacts 2009(5): 0563-0563
DOI: 10.1055/s-0029-1216585
DOI: 10.1055/s-0029-1216585
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Two-Carbon Homologation of Hemiaminal Ethers Using Enecarbamates
M. Terada*, K. Machioka, K. Sorimachi
Tohoku University, Sendai, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
22. April 2009 (online)
Significance
Hemiaminal ethers 2 were used as substrates for two-carbon homologation with enecarbamates 3. Employing chiral phosphoric acids 1 as catalysts, hemiaminal products 4 were obtained in moderate to high yield with high enantioselectivity. The more problematic reaction with aliphatic hemiaminal ethers was solved by using enecarbamates with the more electron-withdrawing trichloroethoxycarbonyl group. The method was shown to be compatible with α-methyl-substituted enecarbamates giving syn or anti product depending on the geometry of the starting enecarbamate.