A NOVEL HIGHLY STEREOSELECTIVE SYNTHESIS OF PYRROLIDINES AND THEIR DERIVATIVES THROUGH THERMAL CYCLIZATION REACTION OF N-[BIS(TRIMETHYLSILYL)METHYL]-1-AZA-1,3-DIENES

被引：13
作者：
PALOMO, C
AIZPURUA, JM
GARCIA, JM
LEGIDO, M
机构：
来源：
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS | 1991年 / 07期
关键词：
D O I：
10.1039/c39910000524
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The first example of the thermal intramolecular cyclization of N-[bis(trimethylsilyl)methyl]-1-aza-1,3-dienes to give 5-trimethylsilyl-DELTA-2-pyrrolines is reported; two straightforward and highly stereoselective routes to 3,4-disubstituted-5-trimethylsilyl-DELTA-1-pyrrolines and 3,4-disubstituted-2-trimethylsilylpyrrolidines are also described.
引用
收藏
页码：524 / 526
页数：3
相关论文
共 14 条
[1]  
[Anonymous], 1984, COMPREHENSIVE HETERO, DOI [10.1016/b978-008096519-2.00056-4, DOI 10.1016/B978-008096519-2.00056-4]
[2]  
Boger D. L., 1987, HETERO DIELS ALDER M
[3]  
CARRUTHERS W, 1990, CYCLOADDITION REACTI, V3, P269
[4]  
CERVINKA O, 1988, ENAMINES SYNTHESIS S, P441
[5]  
HUISGEN R, 1986, 1 3 DIPOLAR CYCLOADD, V1, P1
[6]   STEREOSELECTIVE MICHAEL ADDITION OF THE IMINES OF ALPHA-AMINO ESTERS IN THE PRESENCE OF LITHIUM BROMIDE 1,8-DIAZABICYCLO[5.4.0]UNDEC-7-ENE [J].
KANEMASA, S ;
UCHIDA, O ;
WADA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (14) :4411-4417
[7]   A FACILE SYNTHESIS OF N-ACYL-2-PYRROLINES [J].
KRAUS, GA ;
NEUENSCHWANDER, K .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (23) :4791-4792
[8]   FLUORIDE-ION MEDIATED PETERSON ALKENATION OF BIS(TRIMETHYLSILYL)METHYLIMINES - A NOVEL SYNTHESIS OF 2-AZA-1,3-DIENES AND N-VINYL-BETA-LACTAMS [J].
LASARTE, J ;
PALOMO, C ;
PICARD, JP ;
DUNOGUES, J ;
AIZPURUA, JM .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (02) :72-74
[9]  
NISHIMURA Y, 1988, STUDIES NATURAL PROD, V1, P227
[10]   A NEW VERSION OF THE PETERSON OLEFINATION USING BIS(TRIMETHYLSILYL)METHYL DERIVATIVES AND FLUORIDE-ION AS CATALYST [J].
PALOMO, C ;
AIZPURUA, JM ;
GARCIA, JM ;
GANBOA, I ;
COSSIO, FP ;
LECEA, B ;
LOPEZ, C .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2498-2503
12