Synthesis and enantioselective rearrangement of 4-amino-substituted cyclopentene oxides

被引：18
|
作者：
O'Brien, P [1 ]
Towers, TD [1 ]
Voith, M [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 44期
关键词：
epoxidation; diastereoselection; rearrangements; enantioselection;
D O I：
10.1016/S0040-4039(98)01821-8
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Several N-mono- and diprotected alkenes have been prepared and the, stereoselectivity of their epoxidation has been investigated: N-monoprotected alkenes give cis epoxides preferentially (due to hydrogen bonding directed epoxidations) whereas N-diprotected alkenes produce trans epoxides exclusively (due to steric effects). Chiral lithium amide base-mediated rearrangement of a cis-monoprotected epoxide generated the corresponding amino-cyclopentenol in good yield and with an enantiomeric excess of 60%. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8175 / 8178
页数：4
相关论文
共 50 条
  • [21] Practical enantioselective synthesis of β-substituted-β-amino esters
    Awasthi, AK
    Boys, ML
    Cain-Janicki, KJ
    Colson, PJ
    Doubleday, WW
    Duran, JE
    Farid, PN
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (14): : 5387 - 5397
  • [22] SYNTHESIS IN CYCLOPENTENYL SERIES - PREPARATION OF CYCLOPENTENYLAMINES - VARIOUSLY SUBSTITUTED 3-AMINO-2-CYCLOPENTENE AND 5-AMINO-2-CYCLOPENTENE
    MARTIN, GJ
    RABILLER, C
    BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1972, (11): : 4419 - &
  • [23] RENAL CLEARANCE OF SUBSTITUTED HIPPURATES IN THE DOG .2. 4-AMINO-SUBSTITUTED, HYDROXY-SUBSTITUTED AND METHOXY-SUBSTITUTED BENZOYLGLYCINES
    RUSSEL, FGM
    WOUTERSE, AC
    VANGINNEKEN, CAM
    JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 1989, 248 (01): : 436 - 446
  • [24] A new route to the synthesis of 4-amino-substituted pyrido[2,3-d]pyrimidin-5-one derivatives
    Komkov A.V.
    Baranin S.V.
    Dmitrenok A.S.
    Kolotyrkina N.G.
    Zavarzin I.V.
    Russian Chemical Bulletin, 2021, 70 (2) : 378 - 382
  • [25] REACTION BEHAVIOR OF 4-AMINO-SUBSTITUTED 1,2-NAPHTHOQUINONES UNDER MANNICH CONDITIONS
    MOHRLE, H
    HERBRUGGEN, GS
    ARCHIV DER PHARMAZIE, 1990, 323 (07) : 433 - 438
  • [26] A new route to the synthesis of 4-amino-substituted pyrido[2,3-d]pyrimidin-5-one derivatives
    Komkov, A. V.
    Baranin, S. V.
    Dmitrenok, A. S.
    Kolotyrkina, N. G.
    Zavarzin, I. V.
    RUSSIAN CHEMICAL BULLETIN, 2021, 70 (02) : 378 - 382
  • [27] Organocatalytic Enantioselective Vinylcyclopropane-Cyclopentene (VCP-CP) Rearrangement
    Garay, Gorka
    Hurtado, Josebe
    Pedron, Manuel
    Garcia, Lorena
    Reyes, Efraim
    Sanchez-Diez, Eduardo
    Tejero, Tomas
    Carrillo, Luisa
    Merino, Pedro
    Vicario, Jose L.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (22)
  • [28] An enantioselective synthesis of the cyclopentene fragment of nucleoside Q
    Kim, KH
    Miller, MJ
    TETRAHEDRON LETTERS, 2003, 44 (24) : 4571 - 4573
  • [29] THE SYNTHESIS OF ALPHA-AMINO-SUBSTITUTED DIPHENYLPHOSPHINE OXIDES
    BROEKHOF, NLJM
    VANELBURG, P
    VANDERGEN, A
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1984, 103 (11): : 312 - 316
  • [30] Probing the chemical interaction space governed by 4-amino-substituted benzenesulfonamides and carbonic anhydrase isoforms
    Rasti, Behnam
    Heravi, Yeganeh Entezari
    RESEARCH IN PHARMACEUTICAL SCIENCES, 2018, 13 (03) : 192 - 204
12345