Asymmetric synthesis of monodentate phosphine ligands based on chiral η6-Cr[arene] templates

被引：56

作者：

Nelson, SG ^{[1
]}

Hilfiker, MA ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 09期

关键词：

D O I：

10.1021/ol990929s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Optically active Cr-complexed arylphosphines are presented as a new class of chiral monodentate phosphine ligand for use in asymmetric catalysis, Asymmetric synthesis of the chiral phosphine ligands 9 is achieved in three steps from the achiral Cr[arene] precursor 3. A variety of ligand structures are accessed from a common synthesis intermediate. The utility of these phosphine ligands in asymmetric catalysis is highlighted in Pd(II)-catalyzed allylic alkylation reactions.

引用

收藏

页码：1379 / 1382

页数：4

相关论文

共 30 条

[21] ASYMMETRIC HOMOGENEOUS HYDROGENATION WITH RHODIUM(I) COMPLEXES OF CHIRAL PHOSPHINES [J].

MORRISON, JD ;

BURNETT, RE ;

AGUIAR, AM ;

MORROW, CJ ;

PHILLIPS, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (05) :1301-&

[22] Asymmetric transition metal-catalyzed allylic alkylations [J].

Trost, BM ;

VanVranken, DL .

CHEMICAL REVIEWS, 1996, 96 (01) :395-422

[23] A MODEL FOR METAL-TEMPLATED CATALYTIC ASYMMETRIC INDUCTION VIA PI-ALLYL FRAGMENTS [J].

TROST, BM ;

MURPHY, DJ .

ORGANOMETALLICS, 1985, 4 (06) :1143-1145

[24] Designing a receptor for molecular recognition in a catalytic synthetic reaction: Allylic Alkylation [J].

Trost, BM .

ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (08) :355-364

[25] NEW CHIRAL PHOSPHINE-LIGANDS CONTAINING (ETA-6-ARENE)CHROMIUM AND CATALYTIC ASYMMETRIC CROSS-COUPLING REACTIONS [J].

UEMURA, M ;

MIYAKE, R ;

NISHIMURA, H ;

MATSUMOTO, Y ;

HAYASHI, T .

TETRAHEDRON-ASYMMETRY, 1992, 3 (02) :213-216

[26] SYNTHESIS AND STRUCTURE OF CR(CO)3 COMPLEXES OF BIPHENYL COMPOUNDS WITH AXIAL CHIRALITY [J].

UEMURA, M ;

NISHIMURA, H ;

KAMIKAWA, K ;

SHIRO, M .

INORGANICA CHIMICA ACTA, 1994, 222 (1-2) :63-70

[27] STEREOSELECTIVE INDUCTION OF AN AXIAL CHIRALITY BY SUZUKI CROSS-COUPLING OF TRICARBONYL(ARENE)CHROMIUM COMPLEXES WITH ARYLBORONIC ACIDS [J].

UEMURA, M ;

KAMIKAWA, K .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (23) :2697-2698

[28] CATALYTIC ASYMMETRIC INDUCTION OF PLANAR CHIRALITY - PALLADIUM-CATALYZED ASYMMETRIC CROSS-COUPLING OF MESO TRICARBONYL(ARENE)CHROMIUM COMPLEXES WITH ALKENYLBORONIC AND ARYLBORONIC ACIDS [J].

UEMURA, M ;

NISHIMURA, H ;

HAYASHI, T .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1994, 473 (1-2) :129-137

[29] SYNTHESIS OF BOTH AXIALLY CHIRAL BIARYLS BY CROSS-COUPLING OF (ARENE)CHROMIUM COMPLEXES WITH NAPHTHYLBORONIC ACIDS AND SUBSEQUENT AXIAL ISOMERIZATION [J].

WATANABE, T ;

KAMIKAWA, K ;

UEMURA, M .

TETRAHEDRON LETTERS, 1995, 36 (37) :6695-6698

[30] Asymmetric [3+2] cycloaddition of 2,3-butadienoates with electron-deficient olefins catalyzed by novel chiral 2,5-dialkyl-7-phenyl-7-phosphabicyclo[2.2.1]heptanes [J].

Zhu, GX ;

Chen, ZG ;

Jiang, QZ ;

Xiao, DM ;

Cao, P ;

Zhang, XM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (16) :3836-3837