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 50 条
[31]   [2,3] SIGMATROPIC REARRANGEMENT OF ALLYLIC NITROXIDES AND SULFOXIDES BY AB-INITIO METHODS [J].
JURSIC, BS .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1995, 209 :118-COMP
[32]   Lewis acid mediated asymmetric [2,3]-sigmatropic rearrangement of allylic amines. Scope and mechanistic investigation [J].
Blid, Jan ;
Panknin, Olaf ;
Tuzina, Pavel ;
Somfai, Peter .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (04) :1294-1300
[33]   Catalytic Enantioselective Allylic Amination of Unactivated Terminal Olefins via an Ene Reaction/[2,3]-Rearrangement [J].
Bao, Hongli ;
Tambar, Uttam K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (45) :18495-18498
[34]   [2,3]-Sigmatropic rearrangement of allylic sulfur ylides derived from trimethylsilyldiazomethane (TMSD) [J].
Aggarwal, VK ;
Ferrara, M ;
Hainz, R ;
Spey, SE .
TETRAHEDRON LETTERS, 1999, 40 (50) :8923-8927
[35]   THE FIRST EXAMPLE OF CHIRALITY TRANSFER IN ALLYLIC TELLUROXIDES - POSSIBLE [2,3]-SIGMATROPIC REARRANGEMENT [J].
CHIBA, T ;
NISHIBAYASHI, Y ;
SINGH, JD ;
OHE, K ;
UEMURA, S .
TETRAHEDRON LETTERS, 1995, 36 (09) :1519-1522
[36]   Diastereoselective rhodium(II)-catalyzed sulfonium ylide formation-[2,3]-sigmatropic rearrangement reaction of chiral non-racemic allylic sulfides [J].
Wee, AGH ;
Shi, Q ;
Wang, ZY ;
Hatton, K .
TETRAHEDRON-ASYMMETRY, 2003, 14 (07) :897-909
[37]   The first example of chirality transfer in allylic telluroxides-possible [2,3]-sigmatropic rearrangement [J].
Chiba, T. ;
Nishibayashi, Y. ;
Singh, J. D. ;
Ohe, K. .
Terra Nova, 1994, 695
[38]   [2,3]-SIGMATROPIC REARRANGEMENT OF ALLYLIC SULFINATE ESTERS - A NOVEL SYNTHESIS OF AGELASIDINE-A ANALOGS [J].
SURYAWANSHI, SN ;
RANI, A ;
BHAKUNI, DS .
INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1991, 30 (12) :1089-1094
[39]   Exploiting organocatalysis: Enantioselective synthesis of vinyl glycines by allylic sulfimide [2,3] sigmatropic rearrangement [J].
Armstrong, Alan ;
Challinor, Lee ;
Moir, Jennifer H. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (28) :5369-5372
[40]   Synthesis of (+/-)-ambrox from (E)-nerolidol and beta-ionone via allylic alcohol [2,3] sigmatropic rearrangement [J].
Barrero, AF ;
Altarejos, J ;
AlvarezManzaneda, EJ ;
Ramos, JM ;
Salido, S .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (06) :2215-2218