Sharpless asymmetric dihydroxylation on an industrial scale

被引:49
|
作者
Ahrgren, L [1 ]
Sutin, L [1 ]
机构
[1] Pharmacia & Upjohn AB, S-75182 Uppsala, Sweden
关键词
D O I
10.1021/op970030v
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
It is shown in this study that the inexpensive N-methylmorpholine N-oxide can be successfully employed as a reoxidant in the Sharpless asymmetric dihydroxylation reaction on a large scale, The reaction of o-isopropoxy-m-methoxystyrene on a 2 kg scale gave the corresponding diol in high yield and high enantiomeric excess. The extension of this synthetic method to other olefins is also presented.
引用
收藏
页码:425 / 427
页数:3
相关论文
共 50 条
  • [21] Sharpless Asymmetric Dihydroxylation: An Impressive Gadget for the Synthesis of Natural Products: A Review
    Mushtaq, Aqsa
    Zahoor, Ameer Fawad
    Bilal, Muhammad
    Hussain, Syed Makhdoom
    Irfan, Muhammad
    Akhtar, Rabia
    Irfan, Ali
    Kotwica-Mojzych, Katarzyna
    Mojzych, Mariusz
    MOLECULES, 2023, 28 (06):
  • [22] ELECTROCHEMICAL OS-CATALYZED ASYMMETRIC DIHYDROXYLATION OF OLEFINS WITH SHARPLESS LIGAND
    TORII, S
    LIU, P
    TANAKA, H
    CHEMISTRY LETTERS, 1995, (04) : 319 - 320
  • [23] Application of Sharpless asymmetric dihydroxylation to thienyl-and benzothienyl acrylates and crotonates
    Bonini, Carlo
    Chiummiento, Lucia
    De Bonis, Margherita
    Funicello, Maria
    Lupattelli, Paolo
    Pandolfo, Rocco
    TETRAHEDRON-ASYMMETRY, 2006, 17 (20) : 2919 - 2924
  • [24] Multipolymer-supported substrate and ligand approach to the sharpless asymmetric dihydroxylation
    Han, H
    Janda, KD
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (16): : 1731 - 1733
  • [25] USE OF THE SHARPLESS ASYMMETRIC DIHYDROXYLATION AS A SUBSTITUTE FOR THE KATSUKI-SHARPLESS ASYMMETRIC EPOXIDATION - AN ALTERNATIVE ROUTE TO VITAMIN-E AND PROSTAGLANDIN INTERMEDIATES
    TAKANO, S
    YOSHIMITSU, T
    OGASAWARA, K
    SYNLETT, 1994, (02) : 119 - 120
  • [26] Application of nanofiltration to re-use the sharpless asymmetric dihydroxylation catalytic system
    Ferreira, Frederico Castelo
    Branco, Luis C.
    Kaushal, Kishor Vernia A.
    Crespo, Joao G.
    Afonso, Carlos A. M.
    TETRAHEDRON-ASYMMETRY, 2007, 18 (14) : 1637 - 1641
  • [27] Sharpless Asymmetric Dihydroxylation on ,-Unsaturated Diazoketones: A New Entry for the Synthesis of Disubstituted Furanones
    Talero, Alexander G.
    Burtoloso, Antonio C. B.
    SYNLETT, 2017, 28 (14) : 1748 - 1752
  • [28] Application of the continuous Sharpless dihydroxylation
    Wöltinger, J
    Henniges, H
    Krimmer, HP
    Bommarius, AS
    Drauz, K
    TETRAHEDRON-ASYMMETRY, 2001, 12 (15) : 2095 - 2098
  • [29] Asymmetric synthesis of (S)- and (R)-norketamine via Sharpless asymmetric dihydroxylation/Ritter amination sequence
    Biermann, Manfred
    Zheng, Guangrong
    Hojahmat, Marhaba
    Moskalev, Nick V.
    Crooks, Peter A.
    TETRAHEDRON LETTERS, 2015, 56 (20) : 2608 - 2610
  • [30] Synthesis of Chiral Acyclic Nucleosides by Sharpless Asymmetric Dihydroxylation: Access to Cidofovir and Buciclovir
    Qin, Tao
    Li, Jian-Ping
    Xie, Ming-Sheng
    Qu, Gui-Rong
    Guo, Hai-Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (24): : 15512 - 15523