Diastereoselective synthesis of 4,5-dihydrofurans by iodoenolcyclisation of 2-allyl-1,3-dicarbonyl compounds

被引：30
|
作者：
Antonioletti, R [1 ]
Malancona, S [1 ]
Bovicelli, P [1 ]
机构：
[1] Univ Roma La Sapienza, CNR, Inst Chim Biomol, Sez Roma,Dipartimento Chim, I-00185 Rome, Italy
来源：
TETRAHEDRON | 2002年 / 58卷 / 43期
关键词：
cyclisation; furans; enols and derivatives;
D O I：
10.1016/S0040-4020(02)01064-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A study of the stereochemical aspects of I-2-induced cyclisation of 2-alkenyl-1,3-dicarbonyl compounds reveals that the iodoenolcyclisation is strictly dependent on the dicarbonyl species and the substituents in the allylic position. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8825 / 8831
页数：7
相关论文
共 50 条
  • [41] Synthesis and reactivity of 2-(porphyrin-2-yl)-1,3-dicarbonyl compounds
    Giuntini, F
    Faustino, MAF
    Neves, MGPMS
    Tomé, AC
    Silva, AMS
    Cavaleiro, JAS
    TETRAHEDRON, 2005, 61 (44) : 10454 - 10461
  • [42] REACTIONS OF 2-METHYLENE-1,3-DICARBONYL COMPOUNDS WITH FURAN
    YAMAUCHI, M
    SHIROTA, M
    WATANABE, T
    HETEROCYCLES, 1990, 31 (09) : 1699 - 1704
  • [43] Synthesis of 2-(dibenzosuberen-5-yl)-1,3-dicarbonyl compounds
    E. S. Spesivaya
    V. V. Konshin
    Dzh. N. Konshina
    Russian Journal of General Chemistry, 2015, 85 : 1412 - 1415
  • [44] Synthesis of 2-(dibenzosuberen-5-yl)-1,3-dicarbonyl compounds
    Spesivaya, E. S.
    Konshin, V. V.
    Konshina, Dzh. N.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2015, 85 (06) : 1412 - 1415
  • [45] 2-CYANO-1,3-DICARBONYL COMPOUNDS WITH ANTIALLERGIC ACTIVITY
    BUCKLE, DR
    CANTELLO, BCC
    SMITH, H
    SPICER, BA
    JOURNAL OF MEDICINAL CHEMISTRY, 1977, 20 (02) : 265 - 269
  • [46] DIRECT SYNTHESIS OF 4-PHENYLTHIO-1,3-DICARBONYL COMPOUNDS BY REGIOSELECTIVE SULFENYLATION OF DIMETALLATED DERIVATIVES
    HIROI, K
    MATSUDA, Y
    SATO, S
    SYNTHESIS-STUTTGART, 1979, (08): : 621 - 622
  • [47] Synthesis of Multi-substituted 4,5-Dihydrofuran Derivatives from (S)-Limonene and 1,3-Dicarbonyl Compounds and their Biological Activities
    Findik, E.
    Dingil, A.
    Karaman, I.
    Budak, Y.
    Ceylan, M.
    E-JOURNAL OF CHEMISTRY, 2009, 6 : S53 - S58
  • [48] SYNTHESIS OF 2-AMINO-4,5-DISUBSTITUTED 3,5-DICYANO-4,5-DIHYDROFURANS
    NASAKIN, OY
    NIKOLAEV, YG
    TERENTYEV, PB
    BULAI, AK
    KALANDARISHVILI, AG
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1985, (08): : 1027 - 1030
  • [49] Enantio- and diastereoselective michael reaction of 1,3-dicarbonyl compounds to nitroolefins catalyzed by a bifunctional thiourea
    Okino, Tomotaka
    Hoashi, Yasutaka
    Furukawa, Tomihiro
    Xu, Xuenong
    Takemoto, Yoshiji
    Journal of the American Chemical Society, 2005, 127 (01): : 119 - 125
  • [50] Gold(I)-Catalyzed One-Pot and Diastereoselective Synthesis of trans-2-Silyl-4,5-dihydrofurans from Propargylsilanes and Aldehydes
    Fernandez, Sergio
    Santamaria, Javier
    Ballesteros, Alfredo
    ORGANIC LETTERS, 2020, 22 (16) : 6590 - 6594
12345