REDUCTIVE CLEAVAGE REACTION OF GAMMA-FUNCTIONALIZED ALPHA,BETA-UNSATURATED ESTERS AND HALOMETHYLS MEDIATED WITH MAGNESIUM IN METHANOL

被引：56

作者：

PAK, CS ^{[1
]}

LEE, E ^{[1
]}

LEE, GH ^{[1
]}

机构：

[1] SEOUL NATL UNIV, COLL NAT SCI, DEPT CHEM, SEOUL 151742, SOUTH KOREA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1993年 / 58卷 / 06期

关键词：

D O I：

10.1021/jo00058a038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.

引用

页码：1523 / 1530

页数：8

共 53 条

[1] THE REDUCTION OF TERTIARY N-STYRYLENAMIDES [J].

AINSCOW, RB ;

BRETTLE, R ;

SHIBIB, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1781-1786

[2] TOTAL SYNTHESIS OF (+)-METHYL PSEUDOMONATE-C FROM CARBOHYDRATES [J].

BEAU, JM ;

ABURAKI, S ;

POUGNY, JR ;

SINAY, P .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (03) :621-622

[3] CARBOCYCLIC COMPOUNDS FROM MONOSACCHARIDES .2. TRANSFORMATIONS IN THE MANNOSE SERIES [J].

BERNET, B ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1979, 62 (07) :2400-2410

[4] CARBOCYCLES FROM MONOSACCHARIDES .3. CONCERNING THE DIASTEREOSELECTIVE FORMATION OF CYCLOPENTANE DERIVATIVES - TRANSFORMATIONS IN THE GALACTOSE SERIES [J].

BERNET, B ;

VASELLA, A .

HELVETICA CHIMICA ACTA, 1979, 62 (07) :2411-2431

[5] EFFICIENT PREPARATION OF ENANTIOMERICALLY PURE CYCLIC AMINOALDITOLS, TOTAL SYNTHESIS OF 1-DEOXYNOJIRIMYCIN AND 1-DEOXYMANNOJIRIMYCIN [J].

BERNOTAS, RC ;

GANEM, B .

TETRAHEDRON LETTERS, 1985, 26 (09) :1123-1126

[6] 7-AROYL-2,3-DIHYDROBENZO[B]FURAN-3-CARBOXYLIC ACIDS AND 7-BENZOYL-2,3-DIHYDROBENZO[B]THIOPHENE-3-CARBOXYLIC ACIDS AS ANALGESIC AGENTS [J].

BOYLE, EA ;

MANGAN, FR ;

MARKWELL, RE ;

SMITH, SA ;

THOMSON, MJ ;

WARD, RW ;

WYMAN, PA .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (06) :894-898

[7] SYNTHESIS OF A CHIRAL BICYCLO [410] ALLYLIC NITRILE VIA REDUCTIVE CYCLIZATION OF A DIENYL NITRILE [J].

BRAISH, TF ;

FUCHS, PL .

SYNTHETIC COMMUNICATIONS, 1985, 15 (07) :549-567

[8] THE SELECTIVE REDUCTION OF ALPHA-BETA-OLEFINIC AMIDES [J].

BRETTLE, R ;

SHIBIB, SM .

TETRAHEDRON LETTERS, 1980, 21 (30) :2915-2916

[9] SELECTIVE REDUCTION OF ALPHA-BETA-OLEFINIC AMIDES AND LACTAMS BY MAGNESIUM AND METHANOL [J].

BRETTLE, R ;

SHIBIB, SM .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (11) :2912-2919

[10] LANTHANIDE NMR SHIFT-REAGENTS AND STEREOCHEMICAL ASSIGNMENTS - STEREOCHEMISTRY IN REDUCTION OF 6-DICYANOMETHYLIDENE AND 6-(1-CYANOETHYLIDENE) DERIVATIVES OF CIS-8A-METHYL-1-DECALONE [J].

CAMPS, P ;

ORTUNO, RM ;

SERRATOSA, F .

TETRAHEDRON, 1976, 32 (21) :2583-2587

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