Synthesis of (E)-1-aryl-1-alkenes via a novel BF3•OEt2-catalyzed Aldol-Grob reaction sequence

被引:31
|
作者
Kabalka, GW [1 ]
Li, NS
Tejedor, D
Malladi, RR
Trotman, S
机构
[1] Univ Tennessee, Dept Chem, Knoxville, TN 37996 USA
[2] Univ Tennessee, Dept Radiol, Knoxville, TN 37996 USA
来源
JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 09期
关键词
D O I
10.1021/jo9822784
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reactions of aromatic aldehydes with ketones in the presence of various acids were examined. The reactions generate (E)-1-aryl-1-alkenes in the presence of boron trifluoride diethyl etherate in nonnucleophilic solvents.
引用
收藏
页码:3157 / 3161
页数:5
相关论文
共 50 条
  • [41] BF3•OEt2-Promoted Synthesis of 2,3-Metallocenocyclohexanones: A 1,2-Hydride Shift and Cationic Cyclization Strategy
    He, Congfa
    Wang, Jie
    Gu, Zhenhua
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (16): : 7865 - 7875
  • [42] Synthesis of novel hybrid steroid dimers by BF3•Et2O-catalyzed aldol condensation of 2-formyl-estradiol diacetate and steroid sapogenins
    Ramos-Enriquez, Manuel A.
    Iglesias-Arteaga, Martin A.
    STEROIDS, 2017, 128 : 46 - 49
  • [43] A Novel and Regiospecific Synthesis of 1-Aryl-1H-benzotriazoles via Copper(I)-Catalyzed Intramolecular Cyclization Reaction
    Liu, Qi-Lun
    Wen, Di-Di
    Hang, Chen-Chen
    Li, Qiu-Lian
    Zhu, Yong-Ming
    HELVETICA CHIMICA ACTA, 2010, 93 (07) : 1350 - 1354
  • [44] Synthesis of dimeric spirostanols linked through a 1,4-dimethylidenebenzene moiety by double BF3•Et2O-catalyzed aldol condensation of steroid sapogenins and terephtalaldehyde
    Ramos-Enriquez, Manuel A.
    Rarova, Lucie
    Iglesias-Arteaga, Martin A.
    STEROIDS, 2018, 140 : 58 - 61
  • [46] Synthesis of Novel 5,6-Dihydropyrrolo[2,1-a]isoquinolines via Grob Reaction between (E)-1,1,1-Trifluoro-3-nitro-2-butene and 3,4-Dihydroisoquinolines
    Korotaev, Vladislav Y.
    Sosnovskikh, Vyacheslav Y.
    Barkov, Alexey Y.
    Slepukhin, Pavel A.
    Shklyaev, Yurii V.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2012, 49 (04) : 856 - 860
  • [47] The BF3•Et2O-catalyzed reaction of 1,2-bis[(trimethylsilyl)oxy]cyclobutene and analogues with aromatic ketones
    Crane, SN
    Burnell, DJ
    JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04): : 1352 - 1355
  • [48] An efficient synthesis of 2-(1-(E)-alkenyl)phenylphosphonates via Suzuki reaction of aryl nonaflates with (E)-1-alkenylboronates
    Peng, Ai-Yun
    Chen, Ba-Tian
    Chen, Pei-Jiang
    JOURNAL OF FLUORINE CHEMISTRY, 2013, 151 : 58 - 62
  • [49] The rapid construction and biological evaluation of densely substituted pyrrolo[1,2-a]indoles via a BF3<middle dot>OEt2-assisted cascade approach
    Mali, Ghanshyam
    Yadav, Vinay Kumar
    Priya, Himani
    Shukla, Manjari
    Pandey, Peeyush
    Kumar, Akhilesh
    Paranjothy, Manikandan
    Bhattacharyya, Sudipta
    Erande, Rohan D.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (48) : 9659 - 9668
  • [50] Synthesis and characterization of novel 1,3-selenazine derivatives.: BF3•Et2O-assisted reaction of primary selenoamides with α,β-unsaturated ketones
    Koketsu, M
    Senda, T
    Yoshimura, K
    Ishihara, H
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (04): : 453 - 456