Rhodium-catalyzed direct C-H addition of 4,4-dimethyl-2-oxazoline to alkenes

被引:46
|
作者
Wiedemann, SH
Bergman, RG [1 ]
Eman, JA
机构
[1] Univ Calif Berkeley, Dept Chem, Ctr New Direct Organ Synth, Berkeley, CA 94720 USA
[2] Univ Calif Berkeley, Lawrence Berkeley Lab, Div Chem Sci, Berkeley, CA 94720 USA
关键词
D O I
10.1021/ol049417q
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the preparation of 2-substituted oxazolines by rhodium-catalyzed coupling of alkenes with 4,4-dimethyl-2-oxazoline is reported. The oxazoline products are obtained in good yield with excellent selectivity for the linear product. A variety of alkene substitution patterns and functional groups are tolerated. This procedure represents an attractive alternative to hydroesterification because it does not involve the manipulation of CO gas.
引用
收藏
页码:1685 / 1687
页数:3
相关论文
共 50 条
  • [1] INOR 55-Scope and mechanism of a rhodium-catalyzed C-H addition of heterocycles to alkenes
    Wiedemann, Sean H.
    Lewis, Jared C.
    Bergman, Robert G.
    Ellman, Jonathan A.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 232
  • [2] Rhodium-catalyzed direct C-H addition of 3,4-dihydroquinazolines to alkenes and their use in the total synthesis of vasicoline
    Wiedemann, SH
    Ellman, JA
    Bergman, RG
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (05): : 1969 - 1976
  • [3] Rhodium-Catalyzed Direct Addition of Aryl C-H Bonds to Nitrosobenzenes at Room Temperature
    Zhou, Bing
    Du, Juanjuan
    Yang, Yaxi
    Feng, Huijin
    Li, Yuanchao
    ORGANIC LETTERS, 2013, 15 (24) : 6302 - 6305
  • [4] Rhodium-catalyzed Direct Coupling of Benzothioamides with Alkenes and Alkynes through Directed C-H Bond Cleavage
    Yokoyama, Yuki
    Unoh, Yuto
    Bohmann, Rebekka Anna
    Satoh, Tetsuya
    Hirano, Koji
    Bolm, Carsten
    Miura, Masahiro
    CHEMISTRY LETTERS, 2015, 44 (08) : 1104 - 1106
  • [5] Rhodium-Catalyzed Direct Addition of Aryl C-H Bonds to N-Sulfonyl Aldimines
    Li, Yang
    Li, Bi-Jie
    Wang, Wen-Hua
    Huang, Wei-Ping
    Zhang, Xi-Sha
    Chen, Kang
    Shi, Zhang-Jie
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) : 2115 - 2119
  • [6] Rhodium-Catalyzed Diastereoselective C-H Activation/[4+2] Annulation of α,β-Unsaturated Amides with Bicyclic Alkenes
    Wang, Yan
    Shi, Sijia
    Zhang, Wei
    Nian, Yong
    Wu, Xiaowei
    ORGANIC LETTERS, 2024, 26 (02) : 483 - 487
  • [7] Rhodium-Catalyzed Allylic C-H Functionalization of Unactivated Alkenes with ?-Diazocarbonyl Compounds
    Sihag, Pinki
    Chakraborty, Trisha
    Jeganmohan, Masilamani
    ORGANIC LETTERS, 2023, : 1257 - 1262
  • [8] Rhodium-catalyzed direct ortho C-H olefination of phenol derivatives
    Feng, Chao
    Loh, Teck-Peng
    CHEMICAL COMMUNICATIONS, 2011, 47 (37) : 10458 - 10460
  • [9] Rhodium-Catalyzed Direct C-H Alkenylation of Indoles with Alkenyl Borates
    Wang, Ze-Tian
    Zheng, Zi-Ang
    Li, Peng-Jie
    Zhou, Chun-Ni
    Cai, Shao-Jun
    Xiao, Biao
    Wang, Liang
    CHINESE JOURNAL OF CHEMISTRY, 2021, 39 (10) : 2823 - 2828
  • [10] Rhodium-Catalyzed Direct C-H Bond Cyanation in Ionic Liquids
    Lv, Songyang
    Li, Yaling
    Yao, Tian
    Yu, Xinling
    Zhang, Chen
    Hai, Li
    Wu, Yong
    ORGANIC LETTERS, 2018, 20 (16) : 4994 - 4997