Further application of an N-Ar axially chiral mimetic-type ligand: Asymmetric Grignard cross-coupling reaction

被引：24

作者：

Horibe, H

Kazuta, K

Kotoku, M

Kondo, K

Okuno, H

Murakami, Y

Aoyama, T

机构：

[1] Toho Univ, Fac Pharmaceut Sci, Funabashi, Chiba 2748510, Japan

[2] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

SYNLETT | 2003年 / 13期

关键词：

N-Ar axis; chiral mimetics; optically active ligand; Grignard cross-coupling; asymmetric Kumada-Corriu reaction;

D O I：

10.1055/s-2003-41485

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel chiral ligand mimicking N-Ar axial chirality, (S)-N-[2-(diphenylphosphanyl)naphthalen-1-yl]-2-(piperidinylmethyl)piperidine, was found to exhibit good enantio selectivity (up to 80% ee) in the asymmetric cross-coupling reaction of 1-phenylethylmagnesium chloride with beta-bromostyrene derivatives. Additionally, this type ligand is appealing, because it allows the synthesis of a wide variety of analogues.

引用

页码：2047 / 2051

页数：5

共 56 条

[11] Hattori T, 1997, ENANTIOMER, V2, P203
[12] Hayashi M, 1997, ENANTIOMER, V2, P293
[13] A NEW CHIRAL FERROCENYLPHOSPHINE LIGAND WITH C2 SYMMETRY - PREPARATION AND USE FOR PALLADIUM-CATALYZED ASYMMETRIC CROSS-COUPLING
HAYASHI, T
YAMAMOTO, A
HOJO, M
ITO, Y
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) : 495 - 496
[14] CHIRAL (BETA-AMINOALKYL)PHOSPHINES - HIGHLY EFFICIENT PHOSPHINE-LIGANDS FOR CATALYTIC ASYMMETRIC GRIGNARD CROSS-COUPLING
HAYASHI, T
KONISHI, M
FUKUSHIMA, M
KANEHIRA, K
HIOKI, T
KUMADA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (13) : 2195 - 2202
[15] CHIRAL BETA-DIMETHYLAMINOALKYLPHOSPHINES - HIGHLY EFFICIENT LIGANDS FOR A NICKEL-COMPLEX CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING REACTION
HAYASHI, T
FUKUSHIMA, M
KONISHI, M
KUMADA, M
[J]. TETRAHEDRON LETTERS, 1980, 21 (01) : 79 - 82
[16] ASYMMETRIC CROSS-COUPLING OF ORGANOZINC REAGENTS WITH ALKENYL BROMIDES CATALYZED BY A CHIRAL FERROCENYLPHOSPHINE PALLADIUM COMPLEX
HAYASHI, T
HAGIHARA, T
KATSURO, Y
KUMADA, M
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1983, 56 (01) : 363 - 364
[17] OPTICALLY-ACTIVE ALLYLSILANES .10. ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .3. PREPARATION OF OPTICALLY-ACTIVE ALLYLSILANES BY PALLADIUM-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING
HAYASHI, T
KONISHI, M
OKAMOTO, Y
KABETA, K
KUMADA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (20) : 3772 - 3781
[18] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .2. NICKEL-CATALYZED AND PALLADIUM-CATALYZED ASYMMETRIC GRIGNARD CROSS-COUPLING
HAYASHI, T
KONISHI, M
FUKUSHIMA, M
MISE, T
KAGOTANI, M
TAJIKA, M
KUMADA, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (01) : 180 - 186
[19] CATALYTIC ASYMMETRIC-SYNTHESIS OF AXIALLY CHIRAL BIARYLS BY PALLADIUM-CATALYZED ENANTIOPOSITION-SELECTIVE CROSS-COUPLING
HAYASHI, T
NIIZUMA, S
KAMIKAWA, T
SUZUKI, N
UOZUMI, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) : 9101 - 9102
[20] ASYMMETRIC-SYNTHESIS CATALYZED BY CHIRAL FERROCENYLPHOSPHINE TRANSITION-METAL COMPLEXES .6. PRACTICAL ASYMMETRIC-SYNTHESIS OF 1,1'-BINAPHTHYLS VIA ASYMMETRIC CROSS-COUPLING WITH A CHIRAL [(ALKOXYALKYL)FERROCENYL]MONOPHOSPHINE NICKEL-CATALYST
HAYASHI, T
HAYASHIZAKI, K
KIYOI, T
ITO, Y
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (24) : 8153 - 8156

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