GENERATION OF NITRILE OXIDES THROUGH O-METALATION OF HYDROXIMOYL CHLORIDES - CHELATION-CONTROLLED SYN-SELECTIVE CYCLOADDITION OF NITRILE OXIDES TO ALPHA-SUBSTITUTED ALLYL ALCOHOLS

被引：52

作者：

KANEMASA, S ^{[1
]}

KOBAYASHI, S ^{[1
]}

NISHIUCHI, M ^{[1
]}

YAMAMOTO, H ^{[1
]}

WADA, E ^{[1
]}

机构：

[1] KYUSHU UNIV,INTERDISCIPLINARY GRAD SCH ENGN SCI,DEPT MOLEC SCI & TECHNOL,KASUGA 816,JAPAN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 44期

关键词：

D O I：

10.1016/0040-4039(91)80171-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New generation of nitrile oxides by treatment of hydroximoyl chlorides with organometallics is reported. Thier cycloadditions to the allyl alcohols bearing a chiral center at the 1-position proceed in a syn-selective manner, providing the first example of stereocontrol of 1,3-dipolar cycloaddition by the aid of metal chelation.

引用

页码：6367 / 6370

页数：4

共 55 条

[1] STEREOSELECTIVE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION TO CHIRAL ALLYL ETHERS [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (08) :529-530

[2] DIASTEREOSELECTIVE NITRILE OXIDE CYCLO-ADDITIONS TO CHIRAL ALLYL ETHERS DERIVED FROM 1,1-DITHIO-3-BUTEN-2-OLS [J].

ANNUNZIATA, R ;

CINQUINI, M ;

COZZI, F ;

RAIMONDI, L .

TETRAHEDRON, 1988, 44 (14) :4645-4652

[3] THE INTRAMOLECULAR NITRILE OXIDE CYCLOADDITION ROUTE TO FORSKOLIN [J].

BARALDI, PG ;

BARCO, A ;

BENETTI, S ;

POLLINI, GP ;

POLO, E ;

SIMONI, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1986, (10) :757-758

[4] INTERACTIVITY OF CHIRAL CATALYSTS AND CHIRAL AUXILIARIES IN THE CYCLOADDITION OF ACTIVATED DIENES WITH ALDEHYDES - A SYNTHESIS OF L-GLUCOSE [J].

BEDNARSKI, M ;

DANISHEFSKY, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (22) :7060-7067

[5] TRANSITION STRUCTURES OF THE LEWIS ACID-CATALYZED DIELS-ALDER REACTION OF BUTADIENE WITH ACROLEIN - THE ORIGINS OF SELECTIVITY [J].

BIRNEY, DM ;

HOUK, KN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (11) :4127-4133

[6]

BOGER DL, 1987, HETERO DIELSALDER ME

[7]

CARAMELLA P, 1974, TETRAHEDRON LETT, P229

[8] MODELING CHEMICAL-REACTIVITY .7. THE EFFECT OF A CHANGE IN RATE-LIMITING STEP ON THE STEREOSELECTIVITY OF ELECTROPHILIC ADDITION TO ALLYLIC ALCOHOLS AND RELATED CHIRAL ALKENES [J].

CHAMBERLIN, AR ;

MULHOLLAND, RL ;

KAHN, SD ;

HEHRE, WJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (03) :672-677

[9] PRACTICAL ENANTIOSELECTIVE DIELS-ALDER AND ALDOL REACTIONS USING A NEW CHIRAL CONTROLLER SYSTEM [J].

COREY, EJ ;

IMWINKELRIED, R ;

PIKUL, S ;

XIANG, YB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (14) :5493-5495

[10] DESIGNED CATALYST FOR ENANTIOSELECTIVE DIELS-ALDER ADDITION FROM A C2-SYMMETRICAL CHIRAL BIS(OXAZOLINE)-FE(III) COMPLEX [J].

COREY, EJ ;

IMAI, N ;

ZHANG, HY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (02) :728-729

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