ASYMMETRIC MICHAEL REACTION OF AN ALPHA-CYANO WEINREB AMIDE CATALYZED BY A RHODIUM COMPLEX WITH TRANS-CHELATING CHIRAL DIPHOSPHINE PHTRAP

被引：62

作者：

SAWAMURA, M ^{[1
]}

HAMASHIMA, H ^{[1
]}

SHINOTO, H ^{[1
]}

ITO, Y ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT SYNTHET CHEM & BIOL CHEM,KYOTO 60601,JAPAN

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 36期

关键词：

D O I：

10.1016/0040-4039(95)01295-S

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Asymmetric Michael reaction of N-methoxy-N-methyl-2-cyanopropionamide with vinyl ketones or acrolein in the presence of 0.1-1 mol% of a rhodium catalyst prepared in situ from Rh(acac)(CO)(2) and a trans-chelating chiral diphosphine ligand (S,S)-(R,R)-PhTRAP gave optically active Michael adducts with high enantiomeric excesses (89-94%) in high yields. The adducts with methyl vinyl ketone was transformed into an alpha-cyano aldehyde and ketones with an quarternary asymmetric carbon center through the reaction with LiAlH4 or Grignard reagents.

引用

页码：6479 / 6482

页数：4

共 6 条

[1] N-METHOXY-N-METHYLAMIDES AS EFFECTIVE ACYLATING AGENTS [J].

NAHM, S ;

WEINREB, SM .

TETRAHEDRON LETTERS, 1981, 22 (39) :3815-3818

[2] GOLD(I)-CATALYZED ASYMMETRIC ALDOL REACTION OF N-METHOXY-N-METHYL-ALPHA-ISOCYANOACETAMIDE (ALPHA-ISOCYANO WEINREB AMIDE) - AN EFFICIENT SYNTHESIS OF OPTICALLY-ACTIVE BETA-HYDROXY-ALPHA-AMINO ALDEHYDES AND KETONES [J].

SAWAMURA, M ;

NAKAYAMA, Y ;

KATO, T ;

ITO, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1727-1732

[3] CATALYTIC ASYMMETRIC-SYNTHESIS WITH TRANSCHELATING CHIRAL DIPHOSPHINE LIGAND TRAP - RHODIUM-CATALYZED ASYMMETRIC MICHAEL ADDITION OF ALPHA-CYANO CARBOXYLATES [J].

SAWAMURA, M ;

HAMASHIMA, H ;

ITO, Y .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (21) :8295-8296

[4] ASYMMETRIC MICHAEL REACTION OF ALPHA-CYANO CARBOXYLATES CATALYZED BY A RHODIUM COMPLEX WITH TRANS-CHELATING CHIRAL DIPHOSPHINE PHTRAP [J].

SAWAMURA, M ;

HAMASHIMA, H ;

ITO, Y .

TETRAHEDRON, 1994, 50 (15) :4439-4454

[5] A TRANS-CHELATING CHIRAL DIPHOSPHINE LIGAND - SYNTHESIS OF 2,2''-BIS[1-(DIPHENYLPHOSPHINO)ETHYL]-1,1''-BIFERROCENE AND ITS COMPLEXES WITH PLATINUM(II) AND PALLADIUM(II) [J].

SAWAMURA, M ;

HAMASHIMA, H ;

ITO, Y .

TETRAHEDRON-ASYMMETRY, 1991, 2 (07) :593-596

[6]

SAWAMURA M, UNPUB ORGANOMETALLIC

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