title: Stereodivergent catalytic doubly diastereoselective nitroaldol reactions using heterobimetallic complexes.
abstract: 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.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Tokyo, Japan.
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Sohtome
authors.forename: Yuko
authors.initials: Y
authors.lastname: Kato
authors.forename: Shinya
authors.initials: S
authors.lastname: Handa
authors.forename: Naohiro
authors.initials: N
authors.lastname: Aoyama
authors.forename: Keita
authors.initials: K
authors.lastname: Nagawa
authors.forename: Shigeki
authors.initials: S
authors.lastname: Matsunaga
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: 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
chemical_list: D000447:Aldehydes; D009942:Organometallic Compounds; D007811:Lanthanum; D008094:Lithium; D009584:Nitrogen