SIMPLE STEREOSPECIFIC SYNTHESES OF (R)-2-FLUOROHEXANOIC ACID ETHYL-ESTER

被引：21

作者：

FOCELLA, A

BIZZARRO, F

EXON, C

机构：

[1] Hoffmann-La Roche Inc., Nutley, NJ

来源：

SYNTHETIC COMMUNICATIONS | 1991年 / 21卷 / 21期

关键词：

D O I：

10.1080/00397919108055449

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Simple stereospecific syntheses of 2-fluorohexanoic acid 5 were accomplished by conversion of optically pure L-(+)-norleucine to the optically pure hydroxy acid 3 via the classic diazotization reaction followed by substitution of the hydroxy functionality by the fluoro group. This was accomplished stereospecifically using DAST reagent or more practically by nucleophilic displacement of the corresponding mesyloxy group with fluoride ion.

引用

收藏

页码：2165 / 2170

页数：6

相关论文

共 13 条

[1] ANIONIC ACTIVATION IN POLYMER-SUPPORTED REACTIONS .2. STEREOCHEMICAL STUDIES ON THE INTRODUCTION OF FLUORINE AT CHIRAL CENTERS AND IN BIOLOGICALLY SIGNIFICANT MOLECULES [J].

COLONNA, S ;

RE, A ;

GELBARD, G ;

CESAROTTI, E .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (09) :2248-2252

[2] STEREOSPECIFICITY IN THE TRANSFORMATION OF ALPHA-AMINOACIDS INTO FLUOROACIDS [J].

FAUSTINI, F ;

DEMUNARI, S ;

PANZERI, A ;

VILLA, V ;

GANDOLFI, CA .

TETRAHEDRON LETTERS, 1981, 22 (45) :4533-4536

[3] ORGANIC FLUORINE COMPOUNDS .3. ACTION OF PERCHLORYL FLUORIDE ON SUBSTITUTED ETHYL CYANOACETATES AND ANIMAL TOXICITIES OF FLUORINATED PRODUCTS [J].

GERSHON, H ;

SCHULMAN, SG ;

SPEVACK, AD .

JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (04) :536-&

[4]

Holland G. W., 1978, U. S. Patent Appl, Patent No. [US 4112225A, 4112225]

[5] KINETIC RESOLUTION OF 2-SUBSTITUTED ESTERS CATALYZED BY A LIPASE EX PSEUDOMONAS-FLUORESCENS [J].

KALARITIS, P ;

REGENYE, RW ;

PARTRIDGE, JJ ;

COFFEN, DL .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (03) :812-815

[6]

KALARITIS P, 1990, ORG SYN, V69, P11

[7] SYNTHESIS, ABSOLUTE-CONFIGURATION, AND CIRCULAR-DICHROISM OF THE ENANTIOMERS OF FLUOROSUCCINIC ACID [J].

LOWE, G ;

POTTER, BVL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :2029-2032

[8]

MIDDLETON WJ, 1975, J ORG CHEM, V40, P579

[9]

OLAH GA, 1974, SYNTHESIS-STUTTGART, P652

[10] THE PREPARATION AND SOME CLEAVAGE REACTIONS OF ALKYL AND SUBSTITUTED ALKYL METHANESULPHONATES - THE SYNTHESIS OF FLUORIDES, IODIDES, AND THIOCYANATES [J].

PATTISON, FLM ;

MILLINGTON, JE .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1956, 34 (06) :757-768