AN EFFICIENT SYNTHESIS OF 3-TERT-AMINOPROPANOL DERIVATIVES BY REGIOSELECTIVE RING-OPENING OF TETRAHYDRO-1,3-OXAZINES WITH GRIGNARD-REAGENTS

被引:6
作者
ALBEROLA, A [1 ]
ALVAREZ, MA [1 ]
ANDRES, C [1 ]
GONZALEZ, A [1 ]
PEDROSA, R [1 ]
机构
[1] UNIV VALLADOLID,FAC CIENCIAS,DEPT QUIM ORGAN,E-47011 VALLADOLID,SPAIN
关键词
D O I
10.1080/00397919008052822
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Benzyl tetrahydro-1,3-oxazines react with methy1magnesium iodide, benzylmagnesium bromide,allylmagnesium chloride and phenylmagnesium bromide affording 3-tert-aminopropanol derivatives with excellent yields. By contrast, the same substrates do no react with sodium phenylacetilide or butyllithium, and the corresponding tetrahydro-1,3-oxazinium methiodides are also inert toward Grignard reagents. Copyright © 1990 by Taylor & Francis Group. All rights reserved.
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页码:1149 / 1158
页数:10
相关论文
共 21 条
[1]  
ALBEROLA A, IN PRESS SYNTHESIS
[2]   STEREOSPECIFIC SYNTHESIS OF N-(1-PHENYLETHYL)-2,4,5-TRIPHENYLOXAZOLIDINES [J].
ALCAIDE, B ;
LOPEZMARDOMINGO, C ;
PEREZOSSORIO, R .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (01) :45-48
[3]   ASYMMETRIC-SYNTHESIS .12. STEREOCONTROLLED ELECTROPHILIC-NUCLEOPHILIC ALPHA,ALPHA'-SUBSTITUTION OF THE PYRROLIDINE RING [J].
ARSENIYADIS, S ;
HUANG, PQ ;
PIVETEAU, D ;
HUSSON, HP .
TETRAHEDRON, 1988, 44 (09) :2457-2470
[4]   ADDITION OF ORGANOCUPRATES TO ALPHA-BETA ETHYLENIC CHIRAL OXAZOLIDINES .2. NATURE OF THE NEW INTERMEDIATE-PRODUCTS, MECHANISM, AND STEREOCHEMISTRY [J].
BERLAN, J ;
BESACE, Y .
TETRAHEDRON, 1986, 42 (17) :4767-4776
[5]   ALLYLIC STEREOCENTER DIRECTED ASYMMETRIC CONJUGATE ADDITION - ENANTIOSELECTIVE SYNTHESIS OF 3-ALKYLSUCCINALDEHYDIC ACID METHYL-ESTERS [J].
BERNARDI, A ;
CARDANI, S ;
POLI, G ;
SCOLASTICO, C .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (25) :5041-5043
[6]  
BLAHA K, 1952, CHEM LISTY, V52, P77
[7]  
BOTH H, 1971, CAN J CHEM, V49, P777
[8]  
GERMAN C, 1980, TETRAHEDRON LETT, P3763
[9]  
GLACET C, 1962, B SOC CHIM FR, P2097
[10]   DIPHENYLETHYLAMINES .1. THE PREPARATION OF TERTIARY AMINES BY THE GRIGNARD REACTION [J].
GOODSON, LH ;
CHRISTOPHER, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (01) :358-362