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Synfacts 2010(10): 1192-1192
DOI: 10.1055/s-0030-1258677
DOI: 10.1055/s-0030-1258677
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Organocatalytic Asymmetric α-Aminoxylation of Aldehydes
T. Kano, H. Mii, K. Maruoka*
Kyoto University, Japan
Further Information
Publication History
Publication Date:
22 September 2010 (online)
Significance
The asymmetric secondary amine 1 mediated α-aminoxylation of aldehydes is reported. A combination of the newly developed catalyst 1, stoichiometric amounts of TEMPO, and substoichiometric amounts of benzoyl peroxide as the oxidant furnished an array of the desired α-aminoxy alcohols in high yields and optical purities. The synthetic utility of the products was demonstrated in transformations, such as Pinnick oxidations, diastereoselective Grignard additions as well as a one-pot oxidation-aminoxylation of primary alcohols. Furthermore, the latter transformation supports the mechanistic assumptions involving enamine formation, oxoammonium salt addition and hydrolysis.