HIGHLY DIASTEREOSELECTIVE ALCOHOLYSIS OF SIGMA-SYMMETRICAL DICARBOXYLIC-ACID ANHYDRIDES USING 1-PHENYL-3,3-BIS(TRIFLUOROMETHYL)PROPAN-1,3-DIOL

被引：20

作者：

SUDA, Y

YAGO, S

SHIRO, M

TAGUCHI, T

机构：

[1] TOKYO COLL PHARM, 1432-1 HORINOUCHI, HACHIOJI, TOKYO 19203, JAPAN

[2] RIGAKU CORP, AKISHIMA, TOKYO 196, JAPAN

来源：

CHEMISTRY LETTERS | 1992年 / 03期

关键词：

D O I：

10.1246/cl.1992.389

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Highly diastereoselective alcoholysis of sigma-symmetric dicarboxylic acid anhydrides was performed using 1-phenyl-3,3-bis(trifluoromethyl)propan-1,3-diol. The importance of the geminally trifluoromethylated carbinol moiety for achieving a high degree of chiral induction was confirmed from lower diastereoselectivity with the hydroxyl protected 1,3-diol or with the similar 1,3-diols having hydrocarbon substituents instead of the trifluoromethyl group.

引用

页码：389 / 392

页数：4

共 14 条

[1] STERIC EFFECTS - A STUDY OF A RATIONALLY DESIGNED SYSTEM
BOTT, G
FIELD, LD
STERNHELL, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (17) : 5618 - 5626
[2] ENANTIOSELECTIVE AND ENANTIOCONVERGENT SYNTHESES OF BUILDING-BLOCKS FOR THE TOTAL SYNTHESIS OF CYCLOPENTANOID NATURAL-PRODUCTS
GAIS, HJ
LUKAS, KL
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (02): : 142 - 143
[3] PRACTICAL SYNTHESIS OF AN ENANTIOMERICALLY PURE SYNTHON FOR THE PREPARATION OF MEVINIC ACID ANALOGS
KARANEWSKY, DS
MALLEY, MF
GOUGOUTAS, JZ
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (11) : 3744 - 3747
[4] ENZYMES IN ORGANIC-SYNTHESIS .35. STEREOSELECTIVE PIG-LIVER ESTERASE CATALYZED HYDROLYZES OF 3-SUBSTITUTED GLUTARATE DIESTERS - OPTIMIZATION OF ENANTIOMERIC EXCESS VIA REACTION CONDITIONS CONTROL
LAM, LKP
HUI, RAHF
JONES, JB
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (11) : 2047 - 2050
[5] SYNTHESES OF OPTICALLY-ACTIVE SUBSTANCES FROM THE MESO COMPOUNDS AND THE COMPOUNDS HAVING A PROCHIRAL CARBON-ATOM
NAGAO, Y
FUJITA, E
[J]. JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1984, 42 (07) : 622 - 634
[6] SIMPLIFIED CHIRAL AMINOLYSIS OF PROCHIRAL SIGMA-SYMMETRIC DICARBOXYLIC ANHYDRIDES WITH SODIUM-SALT OF 4(S)-IPTT
NAGAO, Y
HAGIWARA, Y
HASEGAWA, Y
OCHIAI, M
INOUE, T
SHIRO, M
FUJITA, E
[J]. CHEMISTRY LETTERS, 1988, (02) : 381 - 384
[7] Ohno M., 1989, ORGANIC REACTIONS, V37, P1
[8] OHSIMA M, 1987, CHEM LETT, P377
[9] ENANTIOSELECTIVE SYNTHESIS OF S-1452, AN ORALLY ACTIVE POTENT THROMBOXANE-A2 RECEPTOR ANTAGONIST
OHTANI, M
MATSUURA, T
WATANABE, F
NARISADA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (06) : 2122 - 2127
[10] HIGHLY EFFECTIVE AND PRACTICAL ENANTIOSELECTIVE SYNTHESIS OF HALF-ESTERS OF BICYCLO[2.2.1]HEPTANEDICARBOXYLIC ACID
OHTANI, M
MATSUURA, T
WATANABE, F
NARISADA, M
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (13) : 4120 - 4123

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