Mixed La-Li heterobimetallic complexes for tertiary nitroaldol resolution.
A kinetic resolution of tertiary nitroaldols derived from simple ketones is described. Mixed BINOL/biphenol La-Li heterobimetallic complexes gave the best selectivity in retro-nitroaldol reactions of racemic tertiary nitroaldols. By using a mixture of La-Li3-(1a)3 complex (LLB 2a) and La-Li3-(1b)3 (LLB* 2b) complex in a ratio of 2/1, chiral tertiary nitroaldols were obtained in 80-97% ee and 30-47% recovery yield.
Tosaki
Shin-ya
SY
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Hara
Keiichi
K
Gnanadesikan
Vijay
V
Morimoto
Hiroyuki
H
Harada
Shinji
S
Sugita
Mari
M
Yamagiwa
Noriyuki
N
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D000438:Alcohols / Q000737:chemistry / Q000302:isolation & purification*; D006859:Hydrogen / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D007811:Lanthanum / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009284:Naphthols / Q000737:chemistry; D009574:Nitro Compounds / Q000737:chemistry / Q000302:isolation & purification*; D010084:Oxidation-Reduction; D021241:Spectrometry, Mass, Electrospray Ionization
D000438:Alcohols; C406944:BINOL, naphthol; D007659:Ketones; D009284:Naphthols; D009574:Nitro Compounds; D007811:Lanthanum; D006859:Hydrogen; D008094:Lithium