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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 YorkEnantioselective N-Heterocyclic Carbene Catalyzed Mannich Reaction
Y. Kawanaka, E. M. Phillips, K. A. Scheidt*
Northwestern University, Evanston, USA
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Januar 2010 (online)

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.