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Titolo:
Asymmetric hydrogenation catalyzed by (S,S)-R-BisP*-Rh and (R,R)-R-miniPHOS complexes: Scope, limitations, and mechanism
Autore:
Gridnev, ID; Yamanoi, Y; Higashi, N; Tsuruta, H; Yasutake, M; Imamoto, T;
Indirizzi:
Chiba Univ, Fac Sci, Dept Chem, Chiba 2638522, Japan Chiba Univ Chiba Japan 2638522 Fac Sci, Dept Chem, Chiba 2638522, Japan
Titolo Testata:
ADVANCED SYNTHESIS & CATALYSIS
fascicolo: 1, volume: 343, anno: 2001,
pagine: 118 - 136
SICI:
1615-4150(200101)343:1<118:AHCB(A>2.0.ZU;2-C
Fonte:
ISI
Lingua:
ENG
Soggetto:
HIGHLY ENANTIOSELECTIVE HYDROGENATION; P-CHIRAL DIPHOSPHINES; HOMOGENEOUS HYDROGENATION; RHODIUM(I) COMPLEXES; PHOSPHINE-BORANES; ACID-DERIVATIVES; REDUCTIVE AMINATION; MOLECULAR-STRUCTURE; PROCHIRAL ENAMIDES; ALPHA-HYDROXY;
Keywords:
asymmetric catalysis; amino acids; homogeneous catalysis; hydrogenations; P ligands; rhodium;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
62
Recensione:
Indirizzi per estratti:
Indirizzo: Imamoto, T Chiba Univ, Fac Sci, Dept Chem, Chiba 2638522, Japan Chiba Univ Chiba Japan 2638522 ept Chem, Chiba 2638522, Japan
Citazione:
I.D. Gridnev et al., "Asymmetric hydrogenation catalyzed by (S,S)-R-BisP*-Rh and (R,R)-R-miniPHOS complexes: Scope, limitations, and mechanism", ADV SYNTH C, 343(1), 2001, pp. 118-136

Abstract

A new class of chiral C-2-symmetric bis(trialkyl)phosphine ligands has been prepared and used in Rh(I)-catalyzed asymmetric hydrogenation reactions. The Ligands, 1,2-bis(alkylmethylphosphino)ethanes 1 a-g (abbreviated as BisP*, alkyl = t-butyl, 1-adamantyl, 1-methylcyclohexyl, 1,1-diethylpropyl, cyclopentyl, cyclohexyl, isopropyl) and 1,2-bis(alkylmethylphosphino)methanes2 a-d (abbreviated as MiniPHOS, alkyl = t-butyl, cyclohexyl, isopropyl, phenyl) are prepared by a simple synthetic approach based on the air-stable phosphine-boranes. These new ligands give the corresponding Rh(I) complexes,which are effective catalytic precursors for the asymmetric hydrogenation of a representative series of dehydroamino acids and itaconic acid derivatives. Enantioselectivities observed in these hydrogenations are universally high and in many cases exceed 99%. X-Ray characterization of four precatalysts, study of the pressure effects, deuteration experiments, and characterization of the wide series of intermediates in the catalytic cycle are used for the discussion of the possible correlation between the structure of thecatalysts and the outcome of the catalytic asymmetric hydrogenation.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 01/12/20 alle ore 08:01:11