ENANTIOSELECTIVE ESTERIFICATION OF CYCLIC DICARBOXYLIC ANHYDRIDES USING CHIRAL AMINO-ALCOHOLS AS AUXILIARIES

被引：34

作者：

SHIMIZU, M ^{[1
]}

MATSUKAWA, K ^{[1
]}

FUJISAWA, T ^{[1
]}

机构：

[1] MIE UNIV, DEPT CHEM MAT, TSU, MIE 514, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1993年 / 66卷 / 07期

关键词：

D O I：

10.1246/bcsj.66.2128

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Cyclic dicarboxylic anhydrides were enantioselectively esterified with the complex formed from cinchonidine, diethylzinc, and methanol, and the half-esters obtained were readily transformed into lactones via reduction and dehydration.

引用

页码：2128 / 2130

页数：3

共 26 条

[1] STEREOSELECTIVE PIG-LIVER ESTERASE-CATALYZED HYDROLYSIS OF RIGID BICYCLIC MESO-DIESTERS - PREPARATION OF OPTICALLY PURE 4,7-EPOXYTETRA-HYDROPHTHALIDES AND HEXA-HYDROPHTHALIDES [J].

BLOCH, R ;

GUIBEJAMPEL, E ;

GIRARD, C .

TETRAHEDRON LETTERS, 1985, 26 (34) :4087-4090

[2]

CARRENO MC, 1990, TETRAHEDRON LETT, V31, P6653

[3] ENANTIOSELECTIVE AND ENANTIOCONVERGENT SYNTHESES OF BUILDING-BLOCKS FOR THE TOTAL SYNTHESIS OF CYCLOPENTANOID NATURAL-PRODUCTS [J].

GAIS, HJ ;

LUKAS, KL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (02) :142-143

[4] ENANTIODIFFERENTIATING TRANSFORMATION OF PROCHIRAL 1,3,5-PENTANETRIOLS CONTROLLED BY INTRAMOLECULAR VANDERWAALS ATTRACTIONS [J].

HARADA, T ;

WADA, I ;

UCHIMURA, JJ ;

INOUE, A ;

TANAKA, S ;

OKU, A .

TETRAHEDRON LETTERS, 1991, 32 (09) :1219-1222

[5] ENANTIODIFFERENTIATING FUNCTIONALIZATION OF PROCHIRAL DIOLS BY HIGHLY STEREOSELECTIVE RING-CLEAVAGE REACTION OF SPIROACETALS DERIVED FROM L-MENTHONE WITH ALLYLTRIMETHYLSILANE-TITANIUM TETRACHLORIDE [J].

HARADA, T ;

IKEMURA, Y ;

NAKAJIMA, H ;

OHNISHI, T ;

OKU, A .

CHEMISTRY LETTERS, 1990, (08) :1441-1444

[6] CATALYTIC ASYMMETRIC INDUCTION FROM PROCHIRAL CYCLIC ACID ANHYDRIDES USING CINCHONA ALKALOIDS [J].

HIRATAKE, J ;

YAMAMOTO, Y ;

ODA, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (23) :1717-1719

[7] PREPARATION OF (R)-MEVALONIC AND (S)-MEVALONIC ACIDS [J].

HUANG, FC ;

LEE, LFH ;

MITTAL, RSD ;

RAVIKUMAR, PR ;

CHAN, JA ;

SIH, CJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (14) :4144-4145

[8] ASYMMETRIC HYDROLYSIS OF ESTERS BY BIOCHEMICAL METHODS .5. ASYMMETRIC HYDROLYSIS OF PROCHIRAL DIESTERS WITH PIG-LIVER ESTERASE - PREPARATION OF OPTICALLY-ACTIVE INTERMEDIATES FOR THE SYNTHESIS OF (+)-BIOTIN AND (+)-ALPHA-METHYL-3,4-DIHYDROXYPHENYLALANINE [J].

IRIUCHIJIMA, S ;

HASEGAWA, K ;

TSUCHIHASHI, G .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1982, 46 (07) :1907-1910

[9] CATALYTIC ENANTIOTOPOS DIFFERENTIATING DEHYDROGENATION OF PROCHIRAL DIOLS USING RUTHENIUM COMPLEX WITH DIOP [J].

ISHII, Y ;

OSAKADA, K ;

IKARIYA, T ;

SABURI, M ;

YOSHIKAWA, S .

CHEMISTRY LETTERS, 1982, (08) :1179-1182

[10] AN ASYMMETRIC-SYNTHESIS OF 2,4-DIMETHYLVALEROLACTONE AND MEVALONOLACTONE USING CHIRAL BINAPHTHYLDIAMINE DERIVATIVES [J].

KAWAKAMI, Y ;

HIRATAKE, J ;

YAMAMOTO, Y ;

ODA, J .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (12) :779-781

← 1 2 3 →