Stereoselective synthesis of 2 beta-carbomethoxy-3 beta-phenyltropane derivatives. Enhanced stereoselectivity observed for the conjugate addition reaction of phenylmagnesium bromide derivatives with anhydro dichloromethane

被引：23

作者：

Xu, LF

Trudell, ML

机构：

[1] Department of Chemistry, University of New Orleans, New Orleans

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 1996年 / 33卷 / 06期

关键词：

D O I：

10.1002/jhet.5570330676

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The use of dichloromethane as a solvent for the conjugate addition reaction of preformed etheral solutions of phenylmagnesium bromide derivatives with anhydroecgonine methyl ester (2) was found to enhance the stereoselectivity of the reaction and provide the 2 beta-carbomethoxy-3 beta-phenyltropane derivatives 3a-d in high yield.

引用

收藏

页码：2037 / 2039

页数：3

相关论文

共 18 条

[11] CHEMISTRY AND BIOLOGY OF THE 2-BETA-ALKYL-3-BETA-PHENYL ANALOGS OF COCAINE - SUBNANOMOLAR AFFINITY LIGANDS THAT SUGGEST A NEW PHARMACOPHORE MODEL AT THE C-2 POSITION [J].

KOZIKOWSKI, AP ;

SAIAH, MKE ;

JOHNSON, KM ;

BERGMANN, JS .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (16) :3086-3093

[12] SUBSTITUTED 3-PHENYLTROPANE ANALOGS OF COCAINE - SYNTHESIS, INHIBITION OF BINDING AT COCAINE RECOGNITION SITES, AND POSITRON EMISSION TOMOGRAPHY IMAGING [J].

MELTZER, PC ;

LIANG, AY ;

BROWNELL, AL ;

ELMALEH, DR ;

MADRAS, BK .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (07) :855-862

[13] SYNTHESIS AND RECEPTOR-BINDING OF N-SUBSTITUTED TROPANE DERIVATIVES - HIGH-AFFINITY LIGANDS FOR THE COCAINE RECEPTOR [J].

MILIUS, RA ;

SAHA, JK ;

MADRAS, BK ;

NEUMEYER, JL .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (05) :1728-1731

[14] EFFECTS OF REAGENT CONCENTRATIONS AND SOLVENTS ON REACTIONS OF ORGANOMAGNESIUM AND LITHIUM REAGENTS WITH ORTHO-QUINOL ACETATES - DIFFERING REACTION PATHS FROM POLYMERIC GRIGNARDS AND FROM DIALKYLMAGNESIUMS OR MONOMERIC GRIGNARDS [J].

MILLER, B ;

MATJEKA, ER ;

HAGGERTY, JG .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (17) :3121-3127

[15] MODIFICATION OF GRIGNARD REACTION [J].

NELSON, DJ ;

DIFRANCESCO, R ;

PETTERS, D .

JOURNAL OF CHEMICAL EDUCATION, 1977, 54 (10) :648-648

[16] INVERTED STEREOSELECTIVITY IN GRIGNARD ADDITIONS TO CHIRAL ALDEHYDES BY USE OF POLYETHERS [J].

REITSTOEN, B ;

KILAAS, L ;

ANTHONSEN, T .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1986, 40 (06) :440-443

[17] A NEW APPROACH TO CYCLITOLS BASED ON RABBIT MUSCLE ALDOLASE (RAMA) [J].

SCHMID, W ;

WHITESIDES, GM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (26) :9670-9671

[18] DICHLORMETHAN ALS LOSUNGSMITTEL FUR GRIGNARD-REAGENZIEN [J].

VIEHE, HG ;

REINSTEIN, M .

CHEMISCHE BERICHTE-RECUEIL, 1962, 95 (10) :2557-&