Cyclopropanation of 5-(allyloxymethyl)- and 5-(methallyloxymethyl)-5-ethyl-1,3-dioxanes with methyl diazoacetate

被引：0
|
作者：
L. N. Ivanova
A. N. Lobov
A. A. Fatykhov
R. M. Sultanova
S. S. Zlotskii
V. A. Dokichev
机构：
[1] Russian Academy of Sciences,Institute of Organic Chemistry, Ufa Scientific Center
[2] Ufa State University of Oil Engineering,undefined
来源：
Russian Journal of Organic Chemistry | 2011年 / 47卷
关键词：
AcOEt; Cyclopropane Ring; Imidazolium Salt; Allyl Ether; Methyl Trans;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Reactions of 5-(allyloxymethyl)- and 5-(methallyloxymethyl)-5-ethyl-1,3-dioxanes with methyl diazoacetate catalyzed by Rh2(OAc)4 or Cu(OTf)2 in the presence of [bmim]+Cl−, [bmim]+BF4−, and [bmim]+PF6− proceed regioselectively at the C=C bond and lead to the formation of the corresponding cyclopropane-containing 1,3-dioxanes in yields up to 62%.
引用
收藏
页码：1755 / 1760
页数：5
相关论文
共 50 条
  • [31] Biochemical approaches to the synthesis of ethyl 5-(S)-hydroxyhexanoate and 5-(S)-hydroxyhexanenitrile
    Nanduri, VB
    Hanson, RL
    Goswami, A
    Wasylyk, JM
    LaPorte, TL
    Katipally, K
    Chung, HJ
    Patel, RN
    ENZYME AND MICROBIAL TECHNOLOGY, 2001, 28 (7-8) : 632 - 636
  • [32] ROTAMERIC DISTRIBUTION OF 5-HALOMETHYL GROUPS IN 1,3-DIOXANES
    BORREMANS, F
    ANTEUNIS, MJO
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1976, 85 (09): : 673 - 679
  • [33] SYNTHESIS OF 5-(METHYLTHIO)-, 5-(METHANESULFINYL)-, AND 5-(METHANESULFONYL)URACIL AND REACTION OF THE METHYL HYPOBROMITE ADDUCT OF 5-BROMOURACIL WITH CARBONYLMETHYLENE COMPOUNDS
    ANZAI, K
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (10): : 1737 - 1739
  • [34] BROMINATION OF 5-METHYLIDENE-1,3-DIOXANES - INFLUENCE OF THE ACETAL GROUP
    AMADJI, M
    VADECARD, J
    SCHIMMEL, U
    PLE, G
    PLAQUEVENT, JC
    JOURNAL OF CHEMICAL RESEARCH-S, 1995, (09): : 362 - 363
  • [35] THE SYNTHESIS OF 5,5-BIS(ALKOXYMETHYL)-1,3-DIOXANES
    KIREEV, IR
    KANTOR, EA
    VALITOV, RB
    RAKHMANKULOV, DL
    ZHURNAL ORGANICHESKOI KHIMII, 1981, 17 (07): : 1536 - 1539
  • [36] RING INVERSION IN 5,5-DISUBSTITUTED 1,3-DIOXANES
    BOCHKOR, SA
    LAPUKA, LF
    KURMAEVA, ES
    CHALOVA, OB
    ZLOTSKII, SS
    RAKHMANKULOV, DL
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1987, (05): : 607 - 608
  • [37] ASYMMETRIC ISOMERIZATION OF 5-METHYLENE-1,3-DIOXANES TO 5-METHYL-4H-1,3-DIOXINS BY A CHIRAL RUTHENIUM(II) COMPLEX
    FRAUENRATH, H
    KAULARD, M
    SYNLETT, 1994, (07) : 517 - 518
  • [38] CONFORMATION PREFERENCE OF 5-NITRO GROUP IN 1,3-DIOXANES
    ARBUZOV, BA
    KLIMOVITSKII, EN
    YULDASHEVA, LK
    REMIZOV, AB
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1975, 24 (12): : 2632 - 2635
  • [39] NMR EXPERIMENTS ON ACETALS .24. QUANTITATIVE CONFORMATIONAL DATA IN 5-AMINO, AND 5-ACETYL 5-METHYL-1,3-DIOXANES
    COENE, E
    ANTEUNIS, M
    TETRAHEDRON LETTERS, 1970, (08) : 595 - &
  • [40] PREPARATION OF 2-SUBSTITUTED AND 5-SUBSTITUTED-1,3-DIOXANES
    LINDEN, GB
    GOLD, MH
    JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (10): : 1175 - 1176
12345