A heterobimetallic Pd/La/Schiff base complex for anti-selective catalytic asymmetric nitroaldol reactions and applications to short syntheses of β-adrenoceptor agonists

Angewandte Chemie - International Edition

Volumn 47, Issue 17, 2008, Pages 3230-3233

  Handa, Shinya ^a   Nagawa, Keita ^a   Sohtome, Yoshihiro ^a   Matsunaga, Shigeki ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Agonists; Amino alcohols; Asymmetric catalysis; Nitroaldol reaction

Indexed keywords

CHEMICAL REACTIONS; LANTHANUM; PALLADIUM; PALLADIUM COMPOUNDS;

AGONISTS; AMINO ALCOHOLS; ASYMMETRIC CATALYSIS; NITROALDOL REACTION;

SYNTHESIS (CHEMICAL);

ALDEHYDE; BETA ADRENERGIC RECEPTOR STIMULATING AGENT; FUCHSINE; LANTHANUM; PALLADIUM; SCHIFF'S REAGENT;

ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

ADRENERGIC BETA-AGONISTS; ALDEHYDES; CATALYSIS; LANTHANUM; PALLADIUM; ROSANILINE DYES;

EID: 45549083087     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200705617     Document Type: Article

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61. 3 were essential in the present reaction. We assume that cooperative functions of Pd and La metal centers are important for good anti-selectivity and enantioselectivity. For results and discussion, see the Supporting Information.
62. One of the possible reaction mechanisms is as follows; the La-OAr moiety could function as a Brønsted base to deprotonate α proton of the nitroalkane. The La-nitronate would then react with the aldehyde, which is coordinated to the Pd metal center, from TS-A rather than TS-B (see scheme below) to avoid steric repulsion between the R′ group and the Pd/La catalyst, preferentially giving anti-adducts. However, other reaction mechanisms cannot be ruled out at this stage. Detailed mechanistic studies will be reported in due course as a full article. For a recent example utilizing the Brønsted basic property of La-OAr moiety in asymmetric catalysis, see: H. Morimoto, G. Lu, N. Aoyama, S. Matsunaga, M. Shibasaki, J. Am. Chem. Soc. 2007, 129, 9588, and references therein. (Chemical Equation Presented)