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Synfacts 2009(7): 0795-0795
DOI: 10.1055/s-0029-1217306
DOI: 10.1055/s-0029-1217306
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Brønsted Acid Catalyzed Enantioselective Aza-Petasis-Ferrier Rearrangement
M. Terada*, Y. Toda
Tohoku University, Sendai, Japan
Further Information
Publication History
Publication Date:
22 June 2009 (online)
Significance
A catalytic enantioselective aza-Petasis-Ferrier rearrangement has been reported. In the presence of chiral phosphoric acid catalyst 1, racemic vinyl ethers 3 are transformed to β-amino-β-alkylaldehydes 4 with high enantioselectivity and high anti-diastereoselectivity. The protocol is compatible with both aromatic and aliphatic hemiaminal ethers. In addition the chiral phosphoric acid was found to function as an efficient resolving catalyst for racemic hemiaminal ethers.