BETA-TOSYLETHYLAMINE - A USEFUL REAGENT FOR PREPARATION OF N-PROTECTED AMIDES, CARBAMATES, AND RELATED-COMPOUNDS - APPLICATION TO SYNTHESIS OF BETA-LACTAMS

被引:21
作者
DIPIETRO, D
BORZILLERI, RM
WEINREB, SM
机构
[1] Department of Chemistry, Pennsylvania State University, Pennsylvania 16802, University Park
关键词
D O I
10.1021/jo00099a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Readily prepared beta-tosylethylamine (3) can be used to synthesize N-tosylethyl (TSE)-protected amido compounds and beta-lactams, which can be deprotected under mild conditions with potassium tert-butoxide.
引用
收藏
页码:5856 / 5857
页数:2
相关论文
共 12 条
[1]   ELIMINATION AND ADDITION-REACTIONS .27. ADDITION OF AMIDES TO ELECTROPHILIC ALKENES [J].
BATTY, JW ;
HOWES, PD ;
STIRLING, CJM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (14) :1543-1546
[2]  
BOSE AK, 1971, TETRAHEDRON LETT, P3167
[3]   A NEW STRATEGY FOR THE PROTECTION OF DEOXYGUANOSINE DURING OLIGONUCLEOTIDE SYNTHESIS [J].
GAFFNEY, BL ;
JONES, RA .
TETRAHEDRON LETTERS, 1982, 23 (22) :2257-2260
[4]  
GREENE TW, 1991, PROTECTIVE GROUPS OR, P397
[5]   N-TRIMETHYLSILYL IMINES - APPLICATIONS TO THE SYNTHESIS OF BETA-LACTAMS [J].
HA, DC ;
HART, DJ ;
YANG, TK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (17) :4819-4825
[6]   PREPARATION OF PRIMARY AMINES AND 2-AZETIDINONES VIA N-TRIMETHYLSILYL IMINES [J].
HART, DJ ;
KANAI, K ;
THOMAS, DG ;
YANG, TK .
JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (03) :289-294
[7]   THE ESTER ENOLATE IMINE CONDENSATION ROUTE TO BETA-LACTAMS [J].
HART, DJ ;
HA, DC .
CHEMICAL REVIEWS, 1989, 89 (07) :1447-1465
[8]   ELIMINATION-ADDITION .3. NEW PROCEDURES FOR PROTECTION OF AMINO-GROUPS [J].
KADER, AT ;
STIRLING, CJ .
JOURNAL OF THE CHEMICAL SOCIETY, 1964, (JAN) :258-&
[9]   PYRIDYLETHYL - A VERSATILE PROTECTING GROUP .2. THE PROTECTION OF HETEROCYCLIC N-H GROUPS [J].
KATRITZKY, AR ;
KHAN, GR ;
MARSON, CM .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) :641-644
[10]   ANTIBACTERIAL SUBSTANCES RELATED TO PANTOTHENIC ACID [J].
MADINAVEITIA, J ;
MARTIN, AR ;
ROSE, FL ;
SWAIN, G .
BIOCHEMICAL JOURNAL, 1945, 39 (01) :85-91