Direct catalytic asymmetric Mannich-type reaction of beta-keto phosphonate using a dinuclear Ni2-Schiff base complex.
Direct catalytic asymmetric Mannich-type reactions of beta-keto phosphonates are described. A homodinuclear Ni 2-Schiff base complex promoted the reaction at 0 degrees C, giving beta-amino phosphonates in up to 90% yield, 20:1 dr, and 99% ee. Control experiments suggested that two Ni metals are important for achieving high yield and stereoselectivity.
Chen
Zhihua
Z
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo 7-3-1, Bunkyo-ku, Tokyo 113-0033, Japan.
Yakura
Kenichiro
K
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D000588:Amines / Q000138:chemical synthesis*; D018360:Crystallography, X-Ray; D007097:Imines / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism
D000588:Amines; D007097:Imines; D007659:Ketones; D063065:Organophosphonates; D012545:Schiff Bases; D009532:Nickel