Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine:: synthesis of N-allenylsulfenimides

被引:22
作者
Armstrong, A [1 ]
Cooke, RS [1 ]
Shanahan, SE [1 ]
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
关键词
D O I
10.1039/b307722e
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Amination of propargylic sulfides with a ketomalonate-derived oxaziridine under metal free conditions gives N-Boc-N-allenylsulfenimides via [2,3]-sigmatropic rearrangement.
引用
收藏
页码:3142 / 3143
页数:2
相关论文
共 15 条
[1]   Efficient amination of sulfides with a ketomalonate-derived oxaziridine: application to [2,3]-sigmatropic rearrangements of allylic sulfimides [J].
Armstrong, A ;
Cooke, RS .
CHEMICAL COMMUNICATIONS, 2002, (08) :904-905
[2]   A NEW METHOD FOR THE PREPARATION OF TERTIARY BUTYL ETHERS AND ESTERS [J].
ARMSTRONG, A ;
BRACKENRIDGE, I ;
JACKSON, RFW ;
KIRK, JM .
TETRAHEDRON LETTERS, 1988, 29 (20) :2483-2486
[3]   Iron(II)-catalyzed sulfimidation and [2,3]-sigmatropic rearrangement of propargyl Sulfides with tert-butoxycarbonyl azide.: Access to N-allenylsulfenimides [J].
Bacci, JP ;
Greenman, KL ;
Van Vranken, DL .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (12) :4955-4958
[4]   Fe(II)-catalyzed imidation of allyl sulfides and subsequent [2,3]-sigmatropic rearrangement.: Preparation of α-branched N-tert-butyloxycarbonyl (Boc)-protected N-Allylamines [J].
Bach, T ;
Körber, C .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (08) :2358-2367
[5]   Carbon-carbon bond formation in palladium(II)-catalyzed allylic oxidation:: A novel oxidative carbocyclization of allene-substituted olefins [J].
Franzén, J ;
Bäckvall, JE .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (20) :6056-6057
[6]   Iron-catalyzed reaction of propargyl sulfides and trimethylsilyldiazomethane [J].
Prabharasuth, R ;
Van Vranken, DL .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (15) :5256-5258
[7]  
TAMURA Y, 1981, J ORG CHEM, V46, P1732, DOI 10.1021/jo00321a044
[8]   SYNTHESES AND SOME PROPERTIES OF N-UNSUBSTITUTED SULFILIMINES [J].
TAMURA, Y ;
MATSUSHIMA, H ;
MINAMIKAWA, J ;
IKEDA, M .
TETRAHEDRON, 1975, 31 (24) :3035-3040
[9]   Ruthenium-catalyzed two-component addition to form 1,3-dienes: Optimization, scope, applications, and mechanism [J].
Trost, BM ;
Pinkerton, AB ;
Seidel, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12466-12476
[10]   Synthetic studies on CP-225,917 and CP-263,114 [J].
Waizumi, N ;
Itoh, T ;
Fukuyama, T .
TETRAHEDRON LETTERS, 1998, 39 (33) :6015-6018