STEREOSELECTIVE SYNTHESIS OF 7-MEMBERED CARBOCYCLES FROM 2-AMINO-1,3-BUTADIENES AND VINYL CHROMIUM FISCHER-TYPE CARBENES

被引：68

作者：

BARLUENGA, J ^{[1
]}

AZNAR, F ^{[1
]}

MARTIN, A ^{[1
]}

VAZQUEZ, JT ^{[1
]}

机构：

[1] UNIV LA LAGUNA,CTR PROD NAT ORGAN ANTONIO GONZALEZ,E-38206 LA LAGUNA,SPAIN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 37期

关键词：

D O I：

10.1021/ja00142a006

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Seven-membered ring carbocycles are prepared by reaction of easily avaliable 2-amino-1,3-butadienes with vinyl Fischer carbenes. Hydrolysis of the cycloadduct initially formed gives rise to cyclohepta-1,3-diones with total regio- and stereoselectivity in a one-pot process. When 2-aminobutadienes bearing a prolinol derivative as a chiral auxiliary are used, the corresponding cyclic diketones are obtained with very high enantiomeric excesses. The absolute configuration of the stereogenic centers generated was determined with the aid of ROESY and CD measurements.

引用

页码：9419 / 9426

页数：8

共 66 条

[1] OXIDATION OF VICINAL DIOLS TO ALPHA-DICARBONYL COMPOUNDS BY TRIFLUOROACETIC-ANHYDRIDE ACTIVATED DIMETHYLSULFOXIDE [J].

AMON, CM ;

BANWELL, MG ;

GRAVATT, GL .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (22) :4851-4855

[2] ORGANIC SYNTHESES VIA TRANSITION-METAL COMPLEXES .2. 1-CHROMA-1,3-BUTADIENES AND 1-CHROMA-1,3,5-HEXATRIENES FROM (CO)5CR=C(OC2H5)CH3 BY CARBONYL OLEFINATION CATALYZED WITH TRIETHYLAMINE CHLOROTRIMETHYLSILANE [J].

AUMANN, R ;

HEINEN, H .

CHEMISCHE BERICHTE-RECUEIL, 1987, 120 (04) :537-540

[3] 3-COMPONENT INTRAMOLECULAR 2-ALKYNE ANNULATIONS OF FISCHER CARBENE COMPLEXES - NEW STRATEGIES FOR STEROID-SYNTHESIS [J].

BAO, JM ;

WULFF, WD ;

DRAGISICH, V ;

WENGLOWSKY, S ;

BALL, RG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (17) :7616-7630

[4] NEW ROUTES TO SUBSTITUTED TROPONES [J].

BARBOSA, LCA ;

MANN, J ;

WILDE, PD ;

FINCH, MW .

TETRAHEDRON, 1989, 45 (14) :4619-4626

[5] THE FIRST [4+3] ANNULATION OF FISCHER CARBENE COMPLEXES WITH AZADIENES - FACILE SYNTHESIS OF AZEPINES [J].

BARLUENGA, J ;

TOMAS, M ;

BALLESTEROS, A ;

SANTAMARIA, J ;

LOPEZORTIZ, F .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :321-322

[6] TRICYCLIC ETHERS FROM FISCHER VINYLCARBENE COMPLEXES AND BETA-OXYGEN-FUNCTIONALIZED ORGANOLITHIUM COMPOUNDS [J].

BARLUENGA, J ;

MONTSERRAT, JM ;

FLOREZ, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (13) :1068-1070

[7] AN EXPEDITIOUS STEREOSELECTIVE SYNTHESIS OF FUNCTIONALIZED 7-MEMBERED CARBOCYCLES BY REACTION OF 2-AMINOBUTA-1,3-DIENES WITH VINYLCHROMIUM FISCHER TYPE CARBENES [J].

BARLUENGA, J ;

AZNAR, F ;

MARTIN, A ;

GARCIAGRANDA, S ;

SALVADO, MA ;

PERTIERRA, P .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1993, (03) :319-321

[8] VINYLAMINOCARBENES OF GROUP-6 METALS BY METATHESIS REACTION OF 2-AMINO-1,3-BUTADIENES - REACTIVITY TOWARD ELECTRON-DEFICIENT ALKENES [J].

BARLUENGA, J ;

AZNAR, F ;

MARTIN, A .

ORGANOMETALLICS, 1995, 14 (03) :1429-1433

[9] 2-AMINO-1,3-BUTADIENES AS CHIRAL BUILDING-BLOCKS - ENANTIOSELECTIVE SYNTHESIS OF 4-PIPERIDONES, 4-NITROCYCLOHEXANONES, AND 1,3-CYCLOHEPTADIONE DERIVATIVES [J].

BARLUENGA, J ;

AZNAR, F ;

VALDES, C ;

MARTIN, A ;

GARCIAGRANDA, S ;

MARTIN, E .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (10) :4403-4404

[10] CATALYTIC AMINOMERCURATION REACTIONS OF 3-ALKEN-1-YNES - AN IMPROVED METHOD FOR THE SYNTHESIS OF 2-AMINO-1,3-BUTADIENES AND 1-AZA-1,3-BUTADIENES [J].

BARLUENGA, J ;

AZNAR, F ;

VALDES, C ;

CABAL, MP .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (21) :6166-6171

← 1 2 3 4 5 6 7 →