LITHIATION OF N-BOC-2-METHYLTETRAHYDRO-1,3-OXAZINE - A SYNTHETIC EQUIVALENT FOR 1-LITHIO-3-HYDROXY-1-PROPYLAMINE

被引:18
作者
BEAK, P
YUM, EK
机构
[1] Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana
关键词
D O I
10.1021/jo00056a010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A alpha-metalo amine synthetic equivalent of an unactivated primary amine, 1-lithio-3-hydroxy-1-propylamine (7) is provided by the lithiation of N-Boc-2-methyltetrahydro-1,3-oxazine (8) to give 9 which on reaction with electrophiles and hydrolysis gives derivatives of 1-substituted 3-hydroxy-1-propylamines 10-24.
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页码:823 / 824
页数:2
相关论文
共 14 条
[1]   METALATION AND ELECTROPHILIC SUBSTITUTION OF AMINE DERIVATIVES ADJACENT TO NITROGEN - ALPHA-METALLO AMINE SYNTHETIC EQUIVALENTS [J].
BEAK, P ;
ZAJDEL, WJ ;
REITZ, DB .
CHEMICAL REVIEWS, 1984, 84 (05) :471-523
[2]   ALPHA-LITHIOAMINE SYNTHETIC EQUIVALENTS - SYNTHESES OF DIASTEREOISOMERS FROM THE BOC PIPERIDINES [J].
BEAK, P ;
LEE, WK .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (09) :2578-2580
[3]   ENANTIOMERICALLY ENRICHED TERT-BOC-PROTECTED ALPHA-AMINOORGANOLITHIUMS - PREPARATION AND CONFIGURATIONAL STABILITY [J].
CHONG, JM ;
PARK, SB .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (08) :2220-2222
[4]  
FUJI K, 1992, SYNTHESIS-STUTTGART, P852
[5]  
GAWLEY RE, 1991, COMPREHENSIVE ORGANI, V3
[6]  
GAWLEY RE, 1991, COMPREHENSIVE ORGANI, V1
[7]   ALKYLATION OF 2-AZAALLYL ANIONS - A VERSATILE PRIMARY AMINE SYNTHESIS [J].
HORNBACK, JM ;
MURUGAVERL, B .
TETRAHEDRON LETTERS, 1989, 30 (43) :5853-5856
[8]   ASYMMETRIC DEPROTONATIONS - ENANTIOSELECTIVE SYNTHESES OF 2-SUBSTITUTED (TERT-BUTOXYCARBONYL)PYRROLIDINES [J].
KERRICK, ST ;
BEAK, P .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (25) :9708-9710
[9]  
Meyers A. I., 1985, ALDRICHIM ACTA, V18, P59
[10]   STEREOCHEMICAL STUDIES ON CHIRAL, NONCONJUGATED, NITROGEN-SUBSTITUTED CARBANIONS GENERATED BY TIN LITHIUM EXCHANGE [J].
PEARSON, WH ;
LINDBECK, AC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8546-8548