A new preparation of cis-N-sulfonylaziridines from N-sulfonylaldimines using trimethylsilyldiazomethane

被引:29
作者
Hori, R [1 ]
Aoyama, T [1 ]
Shioiri, T [1 ]
机构
[1] Nagoya City Univ, Fac Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan
关键词
trimethylsilyldiazomethane; N-sulfonylaldimine; N-sulfonylaziridine;
D O I
10.1016/S0040-4039(00)01601-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Trimethylsilyldiazomethane smoothly reacts with N-sulfonylaldimines to give 2-substituted N-sulfonyl-3-trimethylsilylaziridines in good yields with high cis selectivity. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9455 / 9458
页数:4
相关论文
共 25 条
[1]  
ANDERSON R, 1991, ADV SILICON CHEM, V1, P303
[2]   Iodine-catalyzed aziridination of alkenes using chloramine-T as a nitrogen source [J].
Ando, T ;
Kano, D ;
Minakata, S ;
Ryu, I ;
Komatsu, M .
TETRAHEDRON, 1998, 54 (44) :13485-13494
[3]   Catalytic asymmetric aziridination with a chiral VAPOL-boron Lewis acid [J].
Antilla, JC ;
Wulff, WD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (21) :5099-5100
[4]  
AOYAMA T, 1989, CHEM PHARM BULL, V37, P253
[5]   Lewis acid-catalyzed synthesis of aziridines [J].
Casarrubios, L ;
Perez, JA ;
Brookhart, M ;
Templeton, JL .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (24) :8358-8359
[6]  
Chemla F, 2000, SYNTHESIS-STUTTGART, P75
[7]   CHEMISTRY OF OXAZIRIDINES .1. SYNTHESIS AND STRUCTURE OF 2-ARENESULFONYL-3-ARYLOXAZIRIDINES - NEW CLASS OF OXAZIRIDINES [J].
DAVIS, FA ;
LAMENDOLA, J ;
NADIR, U ;
KLUGER, EW ;
SEDERGRAN, TC ;
PANUNTO, TW ;
BILLMERS, R ;
JENKINS, R ;
TURCHI, IJ ;
WATSON, WH ;
CHEN, JS ;
KIMURA, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (06) :2000-2005
[8]   COPPER-CATALYZED AZIRIDINATION OF OLEFINS BY (N-(PARA-TOLUENESULFONYL)IMINO)PHENYLIODINANE [J].
EVANS, DA ;
FAUL, MM ;
BILODEAU, MT .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (24) :6744-6746
[9]  
EVANS DA, 1994, J AM CHEM SOC, V116, P2742
[10]   A new synthesis of aziridine-2-carboxylates by reaction of hexahydro-1,3,5-triazines with alkyldiazoacetates in the presence of tin(IV) chloride [J].
Ha, HJ ;
Kang, KH ;
Suh, JM ;
Ahn, YG .
TETRAHEDRON LETTERS, 1996, 37 (39) :7069-7070