Stereoselectivity in addition of phenylselenyl chloride to bicyclo[2.2.1]hept-2-ene derivatives and synthesis of 3'-chloro substituted carbovir

被引：3

作者：

Toyota, A

Nishimura, A

Kaneko, C

机构：

[1] Pharmaceutical Institute, Tohoku University, Aobayama

来源：

HETEROCYCLES | 1997年 / 45卷 / 11期

关键词：

D O I：

10.3987/COM-97-7954

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of phenylselenyl chloride to bicyclo[2.2.1]hept-2-enes was examined and the stereoselectivities have been clarified. The adducts derived from 2-azabicyclo[2.2.1]hept-5-en-3-ones having an electron-withdrawing group at 2-position were converted to 3'-chloro substituted carbovir.

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页码：2105 / 2108

页数：4

相关论文

共 7 条

[1] THE CARBONYL GROUP AS HOMOCONJUGATED ELECTRON DONATING SUBSTITUENT - ABINITIO STO 3G MO CALCULATIONS [J].

CARRUPT, PA ;

VOGEL, P .

TETRAHEDRON LETTERS, 1984, 25 (27) :2879-2882

[2] POTENTIAL USE OF CARBOCYCLIC NUCLEOSIDES FOR THE TREATMENT OF AIDS - CHEMOENZYMATIC SYNTHESES OF THE ENANTIOMERS OF CARBOVIR [J].

EVANS, CT ;

ROBERTS, SM ;

SHOBERU, KA ;

SUTHERLAND, AG .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05) :589-592

[3] FACTORS INFLUENCING THE NATURE OF SELENIRANIUM IONS IN SELENENYL CHLORIDE ADDITIONS TO ALKENES - THE USE OF METHANOL AS SOLVENT [J].

GARRATT, DG ;

KABO, A .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1980, 58 (10) :1030-1041

[4] MOLECULAR MECHANISMS OF ANTIVIRAL RESISTANCE [J].

KIMBERLIN, DW ;

COEN, DM ;

BIRON, KK ;

COHEN, JI ;

LAMB, RA ;

MCKINLAY, M ;

EMINI, EA ;

WHITLEY, RJ .

ANTIVIRAL RESEARCH, 1995, 26 (04) :369-401

[5]

LOWRY TH, 1976, MECH THEORY ORGANIC, P288

[6] REARRANGEMENT OF 2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONES - SYNTHESIS OF CIS-3-AMINOCYCLOPENTANE CARBOXYLIC-ACID DERIVATIVES [J].

PALMER, CF ;

PARRY, KP ;

ROBERTS, SM ;

SIK, V .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (08) :1021-1028

[7] ADDITION OF MOLECULAR FLUORINE TO BICYCLO[2.2.1]HEPT-2-ENE DERIVATIVES AND CONVERSION TO FLUORINE-CONTAINING CARBOCYCLIC NUCLEOSIDES [J].

TOYOTA, A ;

HABUTANI, C ;

KATAGIRI, N ;

KANEKO, C .

TETRAHEDRON LETTERS, 1994, 35 (31) :5665-5668