Synthesis of substituted tetrahydrofurans via intermolecular reactions of γ-chlorocarbanions of 3-substituted 3-chloro-propylphenyl sulfones with aldehydes

被引：6
|
作者：
Brandt, Agnieszka [1 ,2 ]
Wojtasiewicz, Anna [1 ]
Sniezek, Marcin [1 ]
Makosza, Mieczyslaw [1 ]
机构：
[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw 42, Poland
[2] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
来源：
TETRAHEDRON | 2010年 / 66卷 / 18期
关键词：
Carbanions; Aldol reaction; Cyclization; STEREOSELECTIVE-SYNTHESIS;
D O I：
10.1016/j.tet.2010.02.006
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Carbanions of 3-substituted-3-chloropropyl phenyl sulfones add to carbonyl groups of aldehydes to produce aldol type adducts that undergo 1,5-intramolecular substitution giving 2,3,5-trisubstituted tetrahydrofurans. The effect of substituents in the 3-position of these sulfones on the relative rates of 1,3-intramolecular substitution of the corresponding gamma-chlorocarbanions and their intramolecular addition are disclosed. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3378 / 3385
页数：8
相关论文
共 50 条
  • [41] Efficient synthesis of 3-substituted pyrimidinones
    Jeong, JU
    Chen, XH
    Rahman, A
    Yamashita, DS
    Luengo, JI
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 227 : U126 - U126
  • [42] A FACILE SYNTHESIS OF 3-SUBSTITUTED INDOLES
    NAGARATHNAM, D
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (04) : 953 - 958
  • [43] Progress in the Synthesis of 3-Substituted Phthaides
    Li, Quancheng
    Jiang, Lan
    Bai, Rui
    Han, Yongkang
    Li, Zhengning
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (09) : 3390 - 3399
  • [44] SYNTHESIS AND PROPERTIES OF 3-SUBSTITUTED POLYPYRROLES
    KAERIYAMA, K
    MASUDA, H
    SYNTHETIC METALS, 1991, 41 (1-2) : 389 - 392
  • [45] A NEW SYNTHESIS OF 3-SUBSTITUTED CHROMANONES
    DARE, P
    VERLICCHI, L
    EXPERIENTIA, 1960, 16 (07): : 301 - 302
  • [46] Synthesis of 3-substituted indole derivatives
    Li Jitai
    Dai Hongguang
    Lin Zhiping
    PROGRESS IN CHEMISTRY, 2007, 19 (05) : 751 - 761
  • [47] PHOTOCHEMICAL REACTIONS OF 3-SUBSTITUTED CYCLOPENTENYL KETONES
    SMITH, AB
    AGOSTA, WC
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (10) : 3289 - 3295
  • [48] PHOTOCYCLOADDITION REACTIONS OF SOME 3-SUBSTITUTED CYCLOHEXENONES
    CANTRELL, TS
    HALLER, WS
    WILLIAMS, JC
    JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (03): : 509 - &
  • [49] SYNTHESIS OF 3-SUBSTITUTED FURANS FROM 3-C-SUBSTITUTED HEXULOSES
    FAYET, C
    GELAS, J
    CARBOHYDRATE RESEARCH, 1986, 155 : 99 - 106
  • [50] GENERAL SYNTHESIS OF 3-(SUBSTITUTED BENZOYL)-3-SUBSTITUTED ALKANOIC ACIDS
    MCEVOY, FJ
    ALLEN, GR
    JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (23): : 4044 - 4048
12345