Kinetic resolution of racemic epoxides using a chiral diamine catalyst

被引:7
|
作者
Gayet, A [1 ]
Andersson, PG [1 ]
机构
[1] Uppsala Univ, Dept Organ Chem, S-75124 Uppsala, Sweden
关键词
kinetic resolution; epoxide rearrangement; allylic alcohol; chiral diamine;
D O I
10.1016/j.tetlet.2005.05.017
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The kinetic resolution of a variety of racemic epoxides has been performed using a chiral bicyclic diamine ligand. Using 5 mol% of catalyst very high selectivity could be achieved; both epoxide and the corresponding allylic alcohol could be obtained in up to 99% ee. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4805 / 4807
页数:3
相关论文
共 50 条
  • [21] Kinetic resolution of racemic cyclic olefins via chiral dioxirane
    Frohn, M
    Zhou, XM
    Zhang, JR
    Tang, Y
    Shi, Y
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (33) : 7718 - 7719
  • [22] Biocatalyzed kinetic resolution of racemic mixtures of chiral α-aminophosphonic acids
    Kozyra, K.
    Brzezinska-Rodak, M.
    Klimek-Ochab, M.
    Zymanczyk-Duda, E.
    JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC, 2013, 91 : 32 - 36
  • [23] DESIGN OF CHIRAL POLYMERS FOR THE KINETIC RESOLUTION OF RACEMIC CONGLOMERATES.
    Zbaida, D.
    Weissbuch, I.
    Shavit-Gati, E.
    Addadi, L.
    Leiserowitz, L.
    Lahav, M.
    Reactive polymers. Ion exchangers, sorbents, 1986, 6 (2-3): : 241 - 253
  • [24] Kinetic resolution of racemic alkoxy oxiranes by chiral lithium amides
    Bigi, A
    Mordini, A
    Thurner, A
    Faigl, F
    Poli, G
    Toke, L
    TETRAHEDRON-ASYMMETRY, 1998, 9 (13) : 2293 - 2299
  • [25] Kinetic resolution of β-hydroxy epoxides promoted by chiral aluminium reagents
    Wang, SH
    Wang, F
    Zhang, FM
    Fan, CA
    Tu, YQ
    Ren, SK
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2005, 25 (10) : 1302 - 1305
  • [26] Efficient Kinetic Resolution of Terminal Epoxides with Phthalimide Using Chiral Salen(Co)(OAc)
    Wang, Chaoyang
    Song, Guangwei
    Zhu, Jintao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (07) : 1142 - 1146
  • [27] Kinetic resolution of racemic α-hydroxyphosphonates by asymmetric esterification using achiral carboxylic acids with pivalic anhydride and a chiral acyl-transfer catalyst
    Shiina, Isamu
    Ono, Keisuke
    Nakahara, Takayoshi
    CHEMICAL COMMUNICATIONS, 2013, 49 (91) : 10700 - 10702
  • [28] The first supported N-pyridinyl proline-derived chiral catalyst for the kinetic resolution of racemic alcohols
    Pelotier, B
    Priem, G
    Campbell, IB
    Macdonald, SJF
    Anson, MS
    SYNLETT, 2003, (05) : 679 - 683
  • [29] A convenient method for the kinetic resolution of racemic 2-hydroxyalkanoates using diphenylacetic anhydride (DPHAA) and a chiral acyl-transfer catalyst
    Nakata, Kenya
    Sekiguchi, Akihiro
    Shiina, Isamu
    TETRAHEDRON-ASYMMETRY, 2011, 22 (16-17) : 1610 - 1619
  • [30] Asymmetric Aminolytic Kinetic Resolution of Racemic Epoxides Using Recyclable Chiral Polymeric Co(III)-Salen Complexes: A Protocol for Total Utilization of Racemic Epoxide in the Synthesis of (R)-Naftopidil and (S)-Propranolol
    Kumar, Manish
    Kureshy, Rukhsana I.
    Shah, Arpan K.
    Das, Anjan
    Khan, Noor-ul H.
    Abdi, Sayed H. R.
    Bajaj, Hari C.
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (18): : 9076 - 9084