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Synfacts 2010(4): 0472-0472
DOI: 10.1055/s-0029-1219517
DOI: 10.1055/s-0029-1219517
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Trisimidazolines in Asymmetric Conjugate Additions
K. Murai, S. Fukushima, S. Hayashi, Y. Takahara, H. Fujioka*
Osaka University, Suita, Japan
Further Information
Publication History
Publication Date:
22 March 2010 (online)
Significance
The authors report the straightforward synthesis of trisimidazoline 1 and its catalytic application in the conjugate addition of β-keto esters to nitroolefins. The products were obtained in high yields and diastereo- and enantioselectivities. The authors proposed different hydrogen-bonding activation modes, out of which the dual activation of the keto ester and the nitro-styrene seems to be most likely. The origin of enantioselectivity, the C 3 symmetry of the catalyst, is presumed to efficiently preorganize the reactants.