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Synfacts 2010(11): 1300-1300
DOI: 10.1055/s-0030-1258790
DOI: 10.1055/s-0030-1258790
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Catalytic Asymmetric Protonation of Ketene Disilyl Acetals
D. Uraguchi, N. Kinoshita, T. Ooi*
Nagoya University, Japan
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
21. Oktober 2010 (online)
![](https://www.thieme-connect.de/media/synfacts/201011/lookinside/thumbnails/10.1055-s-0030-1258790-1.jpg)
Significance
Ooi and co-workers report the design of new chiral P-spiro diaminodioxaphosphonium barfates 2 and demonstrate their potential to catalyze enantioselective protonation reactions. In the presence of catalyst 2 (1 mol%) and 3 as stoichiometric proton source, the ketene disilyl acetals 1 were protonated in an enantioselective manner to give, after chromatography on silica gel, α-chiral α-amino acids 5 in quantitative yields and high enantioselectivities. The use of 4 (2 mol%) was found to be essential to ensure the reproducibility of high enantiomeric ratios.