Oxaziridine-mediated amination of branched allylic sulfides: Stereospecific formation of allylic amine derivatives via [2,3]-sigmatropic rearrangement

被引:32
作者
Armstrong, A [1 ]
Challinor, L
Cooke, RS
Moir, JH
Treweeke, NR
机构
[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England
[2] Organon Newhouse, Newhouse ML1 5SH, Lanark, Scotland
关键词
D O I
10.1021/jo060369s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of branched allylic sulfides with the N-Boc-oxaziridine 1 results in [2,3]-sigmatropic rearrangement of the intermediate allylic N-Boc-sulfimides with a high level of chirality transfer. The first example of formation of a quaternary stereocenter using this transformation is reported.
引用
收藏
页码:4028 / 4030
页数:3
相关论文
共 27 条
[1]   Oxaziridine-mediated amination of primary amines: Scope and application to a one-pot pyrazole synthesis [J].
Armstrong, A ;
Jones, LH ;
Knight, JD ;
Kelsey, RD .
ORGANIC LETTERS, 2005, 7 (04) :713-716
[2]   Amination and [2,3]-sigmatropic rearrangement of propargylic sulfides using a ketomalonate-derived oxaziridine:: synthesis of N-allenylsulfenimides [J].
Armstrong, A ;
Cooke, RS ;
Shanahan, SE .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (18) :3142-3143
[3]   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
[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]  
Bach T, 1999, EUR J ORG CHEM, V1999, P1033
[6]  
BRAVERMAN S, 1971, INT J SULFUR CHEM C, V6, P149
[7]  
Dembech P, 2000, CHEM-EUR J, V6, P1281, DOI 10.1002/(SICI)1521-3765(20000417)6:8<1281::AID-CHEM1281>3.3.CO
[8]  
2-6
[9]   ENANTIOSPECIFIC SYNTHESIS OF (-)-TABTOXININE BETA-LACTAM [J].
DOLLE, RE ;
LI, CS ;
NOVELLI, R ;
KRUSE, LI ;
EGGLESTON, D .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (01) :128-132
[10]   ENANTIOSELECTIVE SYNTHESIS OF (+)-PINIDINE [J].
DOLLE, RE ;
OSIFO, KI ;
LI, CS .
TETRAHEDRON LETTERS, 1991, 32 (38) :5029-5030