Aziridines as a protecting and directing group. Stereoselective synthesis of (+)-bromoxone

被引:25
|
作者
Barros, MT
Matias, PM
Maycock, CD
Ventura, MR
机构
[1] Univ Nova Lisboa, Fac Ciencias & Tecnol, Dept Quim, P-1200 Lisbon, Portugal
[2] Univ Nova Lisboa, Inst Tecnol Quim & Biol, P-2780 Oeiras, Portugal
关键词
D O I
10.1021/ol035576i
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The directing ability of an aziridine group for the epoxidation of adjacent double bonds is demonstrated. The aziridine group is also used to effectively protect a double bond in a cycloenone system for a short synthesis of the title compound.
引用
收藏
页码:4321 / 4323
页数:3
相关论文
共 50 条
  • [21] Stereoselective etherification and asymmetric synthesis of furanomycin from chiral aziridines
    Jung, Jae-Hoon
    Yoon, Doo-Ha
    Lee, Won Koo
    Yook, Cheol-Min
    Ha, Hyun-Joon
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [22] Borane as an efficient directing group. Stereoselective 1,2-addition of organometallic reagents to borane P-stereogenic N-phosphanylimines
    Flores-Gaspar, Areli
    Orgue, Silvia
    Grabulosa, Arnald
    Riera, Antoni
    Verdaguer, Xavier
    CHEMICAL COMMUNICATIONS, 2015, 51 (10) : 1941 - 1944
  • [23] Stereoselective Synthesis of Trisubstituted Aziridines with N-α-Diazoacyl Camphorsultam
    Hashimoto, Takuya
    Nakatsu, Hiroki
    Watanabe, Shogo
    Maruoka, Keiji
    ORGANIC LETTERS, 2010, 12 (08) : 1668 - 1671
  • [24] The Isothiocyanato Moiety: An Ideal Protecting Group for the Stereoselective Synthesis of Sialic Acid Glycosides and Subsequent Diversification
    Mandhapati, Appi Reddy
    Rajender, Salla
    Shaw, Jonathan
    Crich, David
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (04) : 1275 - 1278
  • [25] Synthesis of iodine compounds of the salvarsan group.
    Macallum, AD
    JOURNAL OF THE CHEMICAL SOCIETY, 1926, : 1645 - 1647
  • [26] SYNTHESIS OF SECONDARY AZIRIDINES SUBSTITUTED BY A TRIFLUOROMETHYL GROUP
    QUINZE, K
    LAURENT, A
    MISON, P
    FAURE, R
    JOURNAL OF FLUORINE CHEMISTRY, 1989, 44 (02) : 211 - 232
  • [27] Fmoc*: A more soluble analog of the 9-fluorenylmethoxycarbonyl protecting group.
    Nowick, JS
    Stigers, KD
    Koutroulis, MR
    Chung, DM
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U113 - U113
  • [28] On the utility of S-mesitylsulfinimines for the stereoselective synthesis of chiral amines and aziridines
    Roe, Caroline
    Sola, Toni Moragas
    Sasraku-Neequaye, Leonid
    Hobbs, Heather
    Churcher, Ian
    MacPherson, David
    Stockman, Robert A.
    CHEMICAL COMMUNICATIONS, 2011, 47 (26) : 7491 - 7493
  • [29] Stereoselective Synthesis of Carbohydrate-Derived N-Sulfonyl Aziridines
    Rodriguez-Solla, Humberto
    Concellon, Carmen
    Alvaredo, Noemi
    Llavona, Ricardo
    Garcia-Granda, Santiago
    Rosario Diaz, M.
    Soengas, Raquel G.
    SYNLETT, 2013, 24 (02) : 181 - 184
  • [30] SYNTHESIS OF CONDURITOL-A FROM BENZOQUINONE USING 9-[(BENZYLOXY)METHOXY]ANTHRACENE AS A PROTECTING AND DIRECTING GROUP
    KNAPP, S
    ORNAF, RM
    RODRIQUES, KE
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (16) : 5494 - 5495