A method for rhodium(II)-catalyzed aziridination of olefins

被引：143
|
作者：
Muller, P
Baud, C
Jacquier, Y
机构：
[1] Dept. de Chimie Organique, Univ. de Genève, CH-1211 Genève, 30, Quai Ernest Ansermet
来源：
TETRAHEDRON | 1996年 / 52卷 / 05期
关键词：
D O I：
10.1016/0040-4020(95)00999-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The [Rh-2(OAc)(4)] catalyzed decomposition of (N-(p-nitrobenzenesulfonyl)imino)phenyliodinane (PhI=NNs) in the presence of olefins affords aziridines In yields of 18-85%. The aziridination of cis-beta-methylstyrene (1h) and cis-hex-2-ene (1k) is stereospecific. However, with cis-stilbene (Im) a ca 3:1 mixture of cis- and trans aziridines 2m and 2l is obtained. With chiral catalysts asymmetric inductions in up to 73% ee are obtained.
引用
收藏
页码：1543 / 1548
页数：6
相关论文
共 50 条
  • [1] Rhodium(II)-Catalyzed Enantioselective Intermolecular Aziridination of Alkenes
    Boquet, Vincent
    Nasrallah, Ali
    Dana, Alejandro L.
    Brunard, Erwan
    Di Chenna, Pablo H.
    Duran, Fernando J.
    Retailleau, Pascal
    Darses, Benjamin
    Sircoglou, Marie
    Dauban, Philippe
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (37) : 17156 - 17164
  • [2] Copper-catalyzed aziridination: A new method for asymmetric aziridination of olefins.
    Chan, KY
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U807 - U807
  • [3] Rhodium(II)-catalyzed aziridination of olefins with {[(4-nitrophenyl)sulfonyl]imino}phenyl- λ3-iodane
    Muller, Paul
    Baud, Corine
    Jacquier, Yvan
    Canadian Journal of Chemistry, 1998, 76 (06): : 738 - 750
  • [4] The rhodium(II)-catalyzed aziridination of olefins with {[(4-nitrophenyl)sulfonyl]imino}phenyl-λ3-iodane
    Müller, P
    Baud, C
    Jacquier, Y
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1998, 76 (06): : 738 - 750
  • [5] Rhodium(II)-catalyzed aziridination of allyl-substituted sulfonamides and carbamates
    Padwa, A
    Flick, AC
    Leverett, CA
    Stengel, T
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (19): : 6377 - 6386
  • [6] Chiral rhodium(II,II) dimers catalyzed enantioselective intramolecular aziridination of sulfonamides and carbamates
    Liang, JL
    Yuan, SX
    Chan, PWH
    Che, CM
    TETRAHEDRON LETTERS, 2003, 44 (31) : 5917 - 5920
  • [7] EFFICIENT METHOD FOR AZIRIDINATION OF OLEFINS
    HOGALE, MB
    CHAVAN, PB
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1993, 58 (07) : 1705 - 1710
  • [8] MTO-catalyzed aziridination of olefins.
    Jeon, HJ
    Zhou, HY
    Nguyen, SBT
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1998, 216 : U191 - U191
  • [9] Hydroformylation of olefins catalyzed by transient montomorillonite rhodium (II) catalyst
    Halligudi, SB
    INDIAN JOURNAL OF CHEMICAL TECHNOLOGY, 1997, 4 (03) : 150 - 154
  • [10] Efficient aziridination of olefins catalyzed by mixed-valent dirhodium(II,III) caprolactamate
    Catino, AJ
    Nichols, JM
    Forslund, RE
    Doyle, MP
    ORGANIC LETTERS, 2005, 7 (13) : 2787 - 2790
12345