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 beta-aryl, beta-heteroaryl, and beta-alkenyl nitroalkenes are described. A new homodinuclear Mn(2)(OAc)(2)-Schiff base 1 complex was required to realize high diastereo- and enantioselectivity. Mn(2)(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 beta-aminooxindoles with vicinal quaternary/tertiary carbon stereocenters.
Kato
Yuko
Y
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Furutachi
Makoto
M
Chen
Zhihua
Z
Mitsunuma
Harunobu
H
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D007211:Indoles / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D000078183:Oxindoles; D012545:Schiff Bases / Q000737:chemistry*; D013237:Stereoisomerism
D000475:Alkenes; D007211:Indoles; D009574:Nitro Compounds; D000078183:Oxindoles; D012545:Schiff Bases; C022960:2-oxindole