Stereodivergent catalytic doubly diastereoselective nitroaldol reactions using heterobimetallic complexes.
Stereodivergent construction of three contiguous stereocenters in catalytic doubly diastereoselective nitroaldol reactions of alpha-chiral aldehydes with nitroacetaldehyde dimethyl acetal using two types of heterobimetallic catalysts is described. A La-Li-BINOL (LLB) catalyst afforded anti,syn-nitroaldol products in >20:1-14:1 selectivity, and a Pd/La/Schiff base catalyst afforded complimentary syn,syn-nitroaldol products in 10:1-5:1 selectivity.
Sohtome
Yoshihiro
Y
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Tokyo, Japan.
Kato
Yuko
Y
Handa
Shinya
S
Aoyama
Naohiro
N
Nagawa
Keita
K
Matsunaga
Shigeki
S
Shibasaki
Masakatsu
M
D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D007811:Lanthanum / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D000447:Aldehydes; D009942:Organometallic Compounds; D007811:Lanthanum; D008094:Lithium; D009584:Nitrogen