Asymmetric hydroformylation of conjugated dienes catalysed by [(R)-2-diphenylphosphino-1,1'-dinaphthalen-2'-yl] [(S)-1,1'-dinaphthalene-2,2'-diyl]phosphite-rhodium(I)

被引：55

作者：

Horiuchi, T ^{[1
]}

Ohta, T ^{[1
]}

Nozaki, K ^{[1
]}

Takaya, H ^{[1
]}

机构：

[1] KYOTO UNIV,GRAD SCH ENGN,DEPT CHEM MAT,SAKYO KU,KYOTO 60601,JAPAN

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 02期

关键词：

D O I：

10.1039/cc9960000155

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric hydroformylation of conjugated dienes such as vinylcyclohexene, (E)-phenyl-buta-1,3-diene and 4-methyl-penta-1,3-diene using BINAPHOS-Rh-I complexes as catalysts {(R,S)-BINAPHOS = [(R)-2-diphenylphosphino-1,1'-dinaphthalen-2'-yl] [(S)-1,1'-dinaphthalene-2,2'-diyl]-phosphite} gives optically active beta,gamma-unsaturated aldehydes in high regio- (81-91%) and enantio-selectivities (84-97% ee).

引用

页码：155 / 156

页数：2

共 11 条

[1] THE HYDROFORMYLATION OF CONJUGATED DIENES .6. TERTIARY ARYL-PHOSPHINES AND ARYLALKYL-PHOSPHINES AND SECONDARY ALKYL-PHOSPHINES AND ARYLPHOSPHINES AS LIGANDS IN THE RHODIUM CATALYZED HYDROFORMYLATION REACTION OF CONJUGATED DIENES TO DIALDEHYDES [J].

BAHRMANN, H ;

FELL, B .

JOURNAL OF MOLECULAR CATALYSIS, 1980, 8 (04) :329-337

[2] ADVANCES IN THE HYDROFORMYLATION OF OLEFINS CONTAINING FUNCTIONAL-GROUPS [J].

BOTTEGHI, C ;

GANZERLA, R ;

LENARDA, M ;

MORETTI, G .

JOURNAL OF MOLECULAR CATALYSIS, 1987, 40 (02) :129-182

[3] OPTICALLY-ACTIVE ALDEHYDES VIA HYDROFORMYLATION OF 1,3-DIENES WITH CHIRAL DIPHOSPHINERHODIUM COMPLEXES [J].

BOTTEGHI, C ;

BRANCA, M ;

SABA, A .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 184 (01) :C17-C19

[4] THE ASYMMETRIC HYDROFORMYLATION IN THE SYNTHESIS OF PHARMACEUTICALS [J].

BOTTEGHI, C ;

PAGANELLI, S ;

SCHIONATO, A ;

MARCHETTI, M .

CHIRALITY, 1991, 3 (04) :355-369

[5] THE STEREOCHEMISTRY OF ORGANOMETALLIC COMPOUNDS .28. THE NICKEL-CATALYZED ADDITION OF HYDROGEN-CYANIDE TO ALIPHATIC DIENES [J].

CAMPI, EM ;

ELMES, PS ;

JACKSON, WR ;

LOVEL, CG ;

PROBERT, MKS .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1987, 40 (06) :1053-1061

[6]

CONSIGLIO G, 1982, TOP CURR CHEM, V105, P77

[7] HYDROFORMYLATION OF CONJUGATED DIENES .5. ALIPHATIC TERTIARY PHOSPHINES AND P-SUBSTITUTED PHOSPHOLANES AS CO-CATALYSTS OF RHODIUM-CATALYZED HYDROFORMYLATION OF 1,3-DIENES [J].

FELL, B ;

BAHRMANN, H .

JOURNAL OF MOLECULAR CATALYSIS, 1977, 2 (03) :211-218

[8] ASYMMETRIC HYDROFORMYLATION OF 1,2-DISUBSTITUTED OLEFINS CATALYZED BY CHIRAL PHOSPHINEPHOSPHITE-RHODIUM(I) COMPLEXES [J].

SAKAI, N ;

NOZAKI, K ;

TAKAYA, H .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (04) :395-396

[9] HIGHLY ENANTIOSELECTIVE HYDROFORMYLATION OF OLEFINS CATALYZED BY NEW PHOSPHINEPHOSPHITE-RH(I) COMPLEXES [J].

SAKAI, N ;

MANO, S ;

NOZAKI, K ;

TAKAYA, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) :7033-7034

[10]

STILLE JK, 1991, COMPREHENSIVE ORGANI, V4, P915

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