METALATED ALLYLUREA WITH STERICALLY PROTECTED CARBONYL GROUP AS NOVEL D3-REAGENT

被引:42
作者
HASSEL, T [1 ]
SEEBACH, D [1 ]
机构
[1] UNIV GIESSEN,INST ORGAN CHEM,D-6300 GIESSEN,FED REP GER
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1979年 / 18卷 / 05期
关键词
D O I
10.1002/anie.197903991
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Exclusive reaction at the γ‐position relative to nitrogen takes place between the urea derivative 2, M = MgBr, and electrophiles. The new reagent is readily prepared from 1 and MgBr2·ether and corresponds to a “propionaldehyde‐homoenolate synthon”.2, M = Li, froms α‐ and γ‐substituted products. (Figure Presented.) Copyright © 1979 by Verlag Chemie, GmbH, Germany
引用
收藏
页码:399 / 400
页数:2
相关论文
共 13 条
[1]  
AHLBRECHT H, 1977, CHIMIA, V31, P391
[2]   REACTIVITY OF ALLYLIC ORGANOMETALLIC COMPOUNDS OF LITHIUM, SODIUM, MAGNESIUM, ZINC, CADMIUM AND ALUMINUM - RECENT ADVANCES [J].
COURTOIS, G ;
MIGINIAC, L .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 69 (01) :1-44
[3]   DOUBLE METALIATION OF BENZYLMERCAPTANES AND ALLYLMERCAPTANES - THIOBENZALDEHYDE AND THIOACROLEIN DIANIONS [J].
GEISS, KH ;
SEEBACH, D ;
SEURING, B .
CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (05) :1833-1851
[4]   STERIC CARBONYL PROTECTION METALATION AND CLEAVAGE OF HIGHLY HINDERED UREAS - PRELIMINARY COMMUNICATION [J].
HASSEL, T ;
SEEBACH, D .
HELVETICA CHIMICA ACTA, 1978, 61 (06) :2237-2240
[5]  
LAU PWK, 1978, TETRAHEDRON LETT, P2383
[6]  
MARTIN SF, 1977, TETRAHEDRON LETT, P3925
[7]   MAGNESIUM DERIVATIVE OF THIOACROLEIN DIANION - FACILE ENTRY TO VINYLOXIRANES AND DIVINYLOXIRANES [J].
SEEBACH, D ;
GEISS, KH ;
POHMAKOTR, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (07) :437-437
[8]   METHODS OF REACTIVITY UMPOLUNG [J].
SEEBACH, D .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (04) :239-258
[9]   LITHIO-1,3,5-TRITHIANES GENERATION IN SOLUTION, REACTIONS WITH ELECTROPHILES, AND USE IN NUCLEOPHILIC ACYLATION [J].
SEEBACH, D ;
COREY, EJ ;
BECK, AK .
CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (02) :367-379
[10]  
Seebach D., 1976, J ORGANOMET CHEM LIB, V1, P1