Stereocontrol of metal-catalyzed cycloaddition of carbonyl ylide with N-substituted maleimide

被引：36

作者：

Suga, H ^{[1
]}

Ishida, H ^{[1
]}

Ibata, T ^{[1
]}

机构：

[1] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 560, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 20期

关键词：

D O I：

10.1016/S0040-4039(98)00449-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The CuOTf (20 mol%) or CuCl-Yb(OTf)(3) (5 mol%) catalyzed decomposition of o-(methoxycarbonyl)-alpha-diazoacetophenone in the presence of N-methylmaleimide gave 1,3-dipolar cycloadducts in an endo-selective manner (endo : exo = 94 : 6). On the other hand, the Rh-2(OAc)(4)-catalyzed (5 mol%) reaction gave cycloadducts with exo-selectivity (endo : exo = 11 : 89). (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：3165 / 3166

页数：2

共 11 条

[1] Stereocontrol in intermolecular dirhodium(II)-catalyzed carbonyl ylide formation and reactions. Dioxolanes and dihydrofurans [J].

Doyle, MP ;

Forbes, DC ;

Protopopova, MN ;

Stanley, SA ;

Vasbinder, MM ;

Xavier, KR .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (21) :7210-7215

[2] A highly diastereoselective and enantioselective Ti(OTos)(2)-TADDOLate-catalyzed 1,3-dipolar cycloaddition reaction of alkenes with nitrones [J].

Gothelf, KV ;

Thomsen, I ;

Jorgensen, KA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (01) :59-64

[3] Catalytic enantioselective tandem carbonyl ylide formation-cycloaddition [J].

Hodgson, DM ;

Stupple, PA ;

Johnstone, C .

TETRAHEDRON LETTERS, 1997, 38 (36) :6471-6472

[4] FORMATION AND REACTION OF CARBONYL YLIDES - 1,3-DIPOLAR CYCLO-ADDITION OF 2-BENZOPYRYLIUM-4-OLATES WITH CARBONYL-COMPOUNDS [J].

IBATA, T ;

TOYODA, J .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1985, 58 (06) :1787-1792

[5] THE REACTION OF DIAZO KETONES IN THE PRESENCE OF METAL-CHELATES .8. THE STEREOCHEMISTRY OF THE 1,3-DIPOLAR CYCLOADDITION OF 1-METHOXY-2-BENZOPYRYLIUM-4-OLATES TO ETHYLENIC DIPOLAROPHILES [J].

IBATA, T ;

JITSUHIRO, K ;

TSUBOKURA, Y .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (01) :240-244

[6] REACTION OF DIAZO KETONES IN THE PRESENCE OF METAL-CHELATES .7. 1,3-DIPOLAR CYCLOADDITION OF 1-METHOXYBENZO[C]PYRYLIUM-4-OLATE WITH ACETYLENIC DIPOLAROPHILES [J].

IBATA, T ;

JITSUHIRO, K .

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1979, 52 (12) :3582-3585

[7] LEWIS ACID-CATALYZED NITRONE CYCLOADDITIONS TO BIDENTATE AND TRIDENTATE ALPHA, BETA-UNSATURATED KETONES - HIGH-RATE ACCELERATION, ABSOLUTELY ENDOSELECTIVE AND REGIOSELECTIVE REACTIONS [J].

KANEMASA, S ;

UEMURA, T ;

WADA, E .

TETRAHEDRON LETTERS, 1992, 33 (51) :7889-7892

[8] 1ST SUCCESSFUL METAL COORDINATION CONTROL IN 1,3-DIPOLAR CYCLOADDITIONS - HIGH-RATE ACCELERATION AND REGIOCONTROL AND STEREOCONTROL OF NITRILE OXIDE CYCLOADDITIONS TO THE MAGNESIUM ALKOXIDES OF ALLYLIC AND HOMOALLYLIC ALCOHOLS [J].

KANEMASA, S ;

NISHIUCHI, M ;

KAMIMURA, A ;

HORI, K .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (06) :2324-2339

[9] Cascade processes of metallo carbenoids [J].

Padwa, A ;

Weingarten, MD .

CHEMICAL REVIEWS, 1996, 96 (01) :223-269

[10] Ligand-induced selectivity in the rhodium(II)-catalyzed reactions of alpha-diazo carbonyl compounds [J].

Padwa, A ;

Austin, DJ ;

Hornbuckle, SF .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (01) :63-72

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