Synthesis of bromoallenyl pyrrolidines via 1,4-addition to 1,3-enynes

被引：0
|
作者：
WERNESS Jenny B. [1 ]
TANG WeiPing [2 ]
机构：
[1] Department of Chemistry, University of Wisconsin
[2] School of Pharmacy, University of Wisconsin
来源：
Science China(Chemistry) | 2011年 / 54卷 / 01期
关键词：
halocyclization; halogenation; conjugated enynes; allene; bromoallene; pyrrolidine;
D O I：
暂无
中图分类号：
O621.3 [有机合成化学];
学科分类号：
070303 ; 081704 ;
摘要：
The discovery of the novel reactivity of conjugated enynes,mediated by readily available halogenation reagents,opens a broad range of mechanistically unique pathways for the synthesis of highly functionalized chiral allene derivatives.Bromoallenyl pyrrolidines can be synthesized via 1,4-addition of sulfonamide nitrogen nucleophiles and halogens to conjugated enynes.This process can lead to simultaneous formation of a highly functionalized axially chiral allene and a stereogenic center under economical and environmentally friendly reaction conditions.
引用
收藏
页码：56 / 60
页数：5
相关论文
共 50 条
  • [41] Three-Component Synthesis of Multiple Functionalized Allenes via Copper/Photoredox Dual Catalyzed 1,4-Alkylcyanation of 1,3-Enynes
    Pu, Yue
    Ding, Shumin
    Zhao, Haixia
    Xue, Qiaoli
    Zhang, Heng
    Xie, Xiaotian
    Shang, Yongjia
    Wang, Jian
    ORGANIC LETTERS, 2024, 26 (09) : 1834 - 1839
  • [42] On 1,2-and 1,4-addition I The 1,4-addition of potassium isocyanide
    Michael, A
    Weiner, N
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1937, 59 : 744 - 753
  • [43] Copper-catalyzed 1,4-alkylarylation of 1,3-enynes with masked alkyl electrophiles
    Ye, Changqing
    Li, Yajun
    Zhu, Xiaotao
    Hu, Shengmin
    Yuan, Daqiang
    Bao, Hongli
    CHEMICAL SCIENCE, 2019, 10 (12) : 3632 - 3636
  • [44] Enantioselective Synthesis of Multisubstituted Allenes by Cooperative Cu/Pd-Catalyzed 1,4-Arylboration of 1,3-Enynes
    Liao, Yang
    Yin, Xuemei
    Wang, Xihong
    Yu, Wangzhi
    Fang, Dongmei
    Hu, Lianrui
    Wang, Min
    Liao, Jian
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (03) : 1176 - 1180
  • [45] N-Heterocyclic Carbene-Catalyzed 1,4-Alkylacylation of 1,3-Enynes
    Cai, Yuxing
    Chen, Jiean
    Huang, Yong
    ORGANIC LETTERS, 2021, 23 (23) : 9251 - 9255
  • [46] CYCLOADDITION REACTIONS - MAINLY ABOUT 1,3-AND 1,4-ADDITION
    SASAKI, T
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1971, 29 (09) : 819 - +
  • [47] 1,4-addition of a phosphinidene complex to Cisoid 1,3-dienes
    van Eis, MJ
    de Kanter, FJJ
    de Wolf, WH
    Lammertsma, K
    Bickelhaupt, F
    Lutz, M
    Spek, AL
    TETRAHEDRON, 2000, 56 (01) : 129 - 136
  • [48] 1,4-ADDITION OF REFORMATSKY REAGENT TO 1,3-DIAZA-1,3-BUTADIENES
    MAZUMDAR, SN
    MAHAJAN, MP
    TETRAHEDRON LETTERS, 1990, 31 (29) : 4215 - 4218
  • [49] Regiodivergent sulfonylarylation of 1,3-enynes via nickel/photoredox dual catalysis
    Chen, Ya
    Zhu, Kun
    Huang, Qingqin
    Lu, Yixin
    CHEMICAL SCIENCE, 2021, 12 (40) : 13564 - 13571
  • [50] Efficient synthesis of AG7172 via a diastereoselective 1,4-addition
    Ma, Chunrong
    Tian, Qingping
    Scott, Jill
    Nayyar, Naresh
    Guzman, Mark
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2006, 231
12345