FORMAL [3 + 2] CYCLOADDITION OF BENZYLIC CATIONS WITH ALKENES

被引：79
作者：
ANGLE, SR
ARNAIZ, DO
机构：
[1] Department of Chemistry, University of California, Riverside
来源：
JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 22期
关键词：
D O I：
10.1021/jo00048a029
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.
引用
收藏
页码：5937 / 5947
页数：11
相关论文
共 50 条
  • [21] CYCLOPENTA[B]INDOLES .1. SYNTHESIS OF CYCLOPENTA[B]INDOLES BY FORMAL [3+2] ADDITION OF INDOLYLMETHYL CATIONS TO ALKENES
    HARRISON, CA
    LEINEWEBER, R
    MOODY, CJ
    WILLIAMS, JMJ
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (09): : 1127 - 1130
  • [22] Intramolecular [3+2] Cyclocondensations of Alkenes with Indolidenes and Indolidenium Cations
    Feldman, Ken S.
    Gonzalez, Inanllely Y.
    Glinkerman, Christopher M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (43) : 15138 - 15141
  • [23] Intramolecular [3+2] cyclocondensations of alkenes with indolidenes and indolidenium cations
    Gonzalez, Inanllely
    Glinkerman, Christopher
    Feldman, Ken
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2015, 249
  • [24] Rh(I)-Catalyzed Formal [6+2] Cycloaddition of 4-Allenals with Alkynes or Alkenes in a Tether
    Oonishi, Yoshihiro
    Hosotani, Akihito
    Sato, Yoshihiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (27) : 10386 - 10389
  • [25] Diastereo- and Enantioselective Formal [3+2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay
    Hao, Wei
    Harenberg, Johannes H.
    Wu, Xiangyu
    MacMillan, Samantha N.
    Lin, Song
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (10) : 3514 - 3517
  • [26] [3+2] Cycloaddition of aza-oxyallyl cations with aldehydes
    Jia, Qianfa
    Du, Zhiyun
    Zhang, Kun
    Wang, Jian
    ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (01): : 91 - 94
  • [27] Cyclic Voltammetric Studies on Anodic Cycloaddition Reactions between Electrogenerated Phenoxonium Cations and Alkenes
    Hirose, Kumi
    Kim, Shokaku
    Chiba, Kazuhiro
    ELECTROCHEMISTRY, 2008, 76 (12) : 871 - 873
  • [28] FeBr3-catalyzed Fully Intermolecular [2+2+2] Cycloaddition of Alkenes
    Tomifuji, Rei
    Murano, Shunpei
    Kurahashi, Takuya
    Matsubara, Seijiro
    CHEMISTRY LETTERS, 2021, 50 (12) : 2018 - 2021
  • [29] Cycloaddition of 2-pyridinetellurenyl chloride to alkenes
    Borisov, A. V.
    Matsulevich, Zh V.
    Osmanov, V. K.
    Borisova, G. N.
    Naumov, V. I.
    Mammadova, G. Z.
    Maharramov, A. M.
    Khrustalev, V. N.
    Kachala, V. V.
    RUSSIAN CHEMICAL BULLETIN, 2012, 61 (01) : 91 - 94
  • [30] Formal [4+2] cycloaddition of 3-phenylcyclobutanones with nitriles
    Igarashi, Emiko
    Sakamoto, Kenta
    Yoshimura, Tomoyuki
    Matsuo, Jun-ichi
    TETRAHEDRON LETTERS, 2019, 60 (01) : 13 - 15
12345