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
[21]   STEREOSELECTIVE FORMATION OF ALLYLIC SULFIDES VIA 2 SEQUENTIAL [3,3]-SIGMATROPIC REARRANGEMENTS OF ALLYLIC XANTHATES AND ITS MECHANISTIC ASPECTS [J].
HARANO, K ;
OHIZUMI, N ;
MISAKA, K ;
YAMASHIRO, S ;
HISANO, T .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (03) :619-624
[22]   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
[23]   A new approach to isolevoglucosenone via the 2,3-sigmatropic rearrangement of an allylic selenide [J].
Witczak, ZJ ;
Kaplon, P ;
Kolodziej, M .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 2002, 21 (1-2) :143-148
[24]   OXIDATIVELY ASSISTED HYDROLYSIS OF ALLYLIC IODIDES TO REARRANGED ALLYLIC ALCOHOLS - A NEW EXAMPLE OF [2,3] SIGMATROPIC REARRANGEMENT [J].
YAMAMOTO, S ;
ITANI, H ;
TSUJI, T ;
NAGATA, W .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (09) :2908-2909
[25]   SYNTHESIS, ALKYLATION AND [2,3]-SIGMATROPIC REARRANGEMENT STUDIES OF A NEW ALLYLIC SULFOXIDE [J].
KIRK, GW ;
SULLARDS, CM ;
GOODWIN, TE .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1993, 205 :204-CHED
[26]   From Allylic Sulfoxides to Allylic Sulfenates: Fifty Years of a Never-Ending [2,3]-Sigmatropic Rearrangement [J].
Colomer, Ignacio ;
Velado, Marina ;
Fernandez de la Pradilla, Roberto ;
Viso, Alma .
CHEMICAL REVIEWS, 2017, 117 (24) :14201-14243
[27]   Ab initio study of [2,3] sigmatropic rearrangement of allylic nitroxides and sulfoxides [J].
Jursic, BS .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 1995, 358 :131-138
[28]   Asymmetric Lewis acid-mediated [2,3]-sigmatropic rearrangement of allylic α-amino amides. [J].
Blid, J ;
Somfai, P ;
Brandt, P .
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 :U60-U60
[29]   [2,3]-sigmatropic rearrangement of ylides resulting from the reaction of a diazomethylphosphonate with allylic sulfides.: Synthesis of new α-phosphorylated unsaturated sulfides [J].
Gulea, M ;
Marchand, P ;
Masson, S ;
Saquet, M ;
Collignon, N .
SYNTHESIS-STUTTGART, 1998, (11) :1635-1639
[30]   Tandem Catalytic Allylic Amination and [2,3]-Stevens Rearrangement of Tertiary Amines [J].
Soheili, Arash ;
Tambar, Uttarn K. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (33) :12956-12959