A Homodinuclear Mn(III)2−Schiff Base Complex for Catalytic Asymmetric 1,4-Additions of Oxindoles to Nitroalkenes

Catalytic asymmetric 1,4-additions of 3-substituted oxindoles to β-aryl, β-heteroaryl, and β-alkenyl nitroalkenes are described. A new homodinuclear Mn2(OAc)2−Schiff base 1 complex was required to realize high diastereo- and enantioselectivity. Mn2(OAc)2−1 (1−5 mol %) promoted the 1,4-additions in 9...

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Veröffentlicht in:Journal of the American Chemical Society 2009-07, Vol.131 (26), p.9168-9169
Hauptverfasser: Kato, Yuko, Furutachi, Makoto, Chen, Zhihua, Mitsunuma, Harunobu, Matsunaga, Shigeki, Shibasaki, Masakatsu
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Sprache:eng
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Zusammenfassung:Catalytic asymmetric 1,4-additions of 3-substituted oxindoles to β-aryl, β-heteroaryl, and β-alkenyl nitroalkenes are described. A new homodinuclear Mn2(OAc)2−Schiff base 1 complex was required to realize high diastereo- and enantioselectivity. Mn2(OAc)2−1 (1−5 mol %) promoted the 1,4-additions in 99−83% yield, 96−85% ee, and >30:1−5:1 dr at room temperature, providing useful chiral building blocks for the synthesis of β-aminooxindoles with vicinal quaternary/tertiary carbon stereocenters.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja903566u