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Titolo:
Rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids and theirderivatives to electron deficient olefins
Autore:
Hayashi, T;
Indirizzi:
Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan Kyoto Univ Kyoto Japan 6068502 Sch Sci, Dept Chem, Kyoto 6068502, Japan
Titolo Testata:
SYNLETT
, , anno: 2001,
pagine: 879 - 887
SICI:
0936-5214(2001):<879:RA1OOA>2.0.ZU;2-A
Fonte:
ISI
Lingua:
ENG
Soggetto:
ENANTIOSELECTIVE CONJUGATE ADDITION; OXAZOLINE-PHOSPHITE LIGANDS; ALPHA-CYANO CARBOXYLATES; ORGANOZINC REAGENTS; ALPHA,BETA-UNSATURATED KETONES; ALKENYLBORONIC ACIDS; MICHAEL ADDITIONS; ARYLBORONIC ACIDS; ALDOL REACTIONS; ENONES;
Keywords:
asymmetric catalysis; asymmetric 1,4-addition; rhodium complex; organoboronic acids; electron deficient olefins;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
59
Recensione:
Indirizzi per estratti:
Indirizzo: Hayashi, T Kyoto Univ, Grad Sch Sci, Dept Chem, Kyoto 6068502, Japan KyotoUniv Kyoto Japan 6068502 ept Chem, Kyoto 6068502, Japan
Citazione:
T. Hayashi, "Rhodium-catalyzed asymmetric 1,4-addition of organoboronic acids and theirderivatives to electron deficient olefins", SYNLETT, 2001, pp. 879-887

Abstract

Asymmetric 1,4-arylation and -alkenylation was achieved by use of organoboronic acids or their derivatives in the presence of a rhodium catalyst coordinated with binap ligand. The reaction conditions are unique in that it isusually carried out in an aqueous solvent at 100 degreesC. The scope of this asymmetric addition is very broad, alpha,beta -unsaturated ketones, eaters, 1-alkenylphosphonates, and l-nitroalkenes being efficiently converted into the corresponding optically active 1,4-addition products with over 95% enantioselectivity. The catalytic cycle is proposed to involve the enantioselective addition of aryl- or alkenyl-rhodium intermediate to carbon-carbondouble bond of the electron deficient olefins as a key step.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 04/04/20 alle ore 02:37:40