A Rare Alder-ene Cycloisomerization of 1,6-Allenynes

被引：6
|
作者：
Joyce, Liam M. [1 ]
Drew, Melanie A. [1 ]
Tague, Andrew J. [1 ]
Thaima, Thanaphat [1 ]
Gouranourimi, Ali [2 ]
Ariafard, Alireza [2 ]
Pyne, Stephen G. [1 ]
Hyland, Christopher J. T. [1 ]
机构：
[1] Univ Wollongong, Sch Chem & Biomol Sci, Mol Horizons Res Inst, Wollongong, NSW 2522, Australia
[2] Univ Tasmania, Sch Phys Sci, Hobart, Tas 7018, Australia
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2022年 / 28卷 / 12期
基金：
澳大利亚研究理事会;
关键词：
1; 6-allenyne; Alder-ene; cycloisomerization; lactam; computations; INTRAMOLECULAR 2+2 CYCLOADDITION; GOLD-CATALYZED CYCLOISOMERIZATION; ALLENE; CYCLIZATION; ACTIVATION; CONSTRUCTION; SUBSTITUENT; LACTONES; NITROGEN;
D O I：
10.1002/chem.202104022
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Thermally induced cycloisomerization reactions of 1,6-allenynes gives alpha-methylene-gamma-lactams via intramolecular Alder-ene reactions. The mechanism is supported by computational and deuterium labelling studies. This thermal, non-radical method enables the discovery of a hitherto unknown route that proceeds via a divergent mechanism distinct from the previous [2+2] cycloisomerization manifold.
引用
收藏
页数：5
相关论文
共 50 条
  • [31] Alder-ene reaction of 3-methyl-3-cyanocyclopropene with monoterpenes
    Ashirov, Roman V.
    Balandina, Alsu A.
    Kharlamov, Sergey V.
    Appolonova, Svetlana A.
    Figadere, Bruno
    Latypov, Shamil K.
    Plemenkov, Vitali V.
    LETTERS IN ORGANIC CHEMISTRY, 2006, 3 (09) : 670 - 673
  • [32] A nickel(ii)-catalyzed asymmetric intramolecular Alder-ene reaction of 1,7-dienes
    Liu, Wen
    Zhou, Pengfei
    Lang, Jiawen
    Dong, Shunxi
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMICAL COMMUNICATIONS, 2019, 55 (31) : 4479 - 4482
  • [33] Reactivity of Enyne-Allenes Generated via an Alder-Ene Reaction
    Vo, Duy-Viet
    Su, Siyuan
    Karmakar, Rajdip
    Lee, Daesung
    ORGANIC LETTERS, 2024, 26 (07) : 1299 - 1303
  • [34] Alder-Ene Reactions of Arynes (vol 15, pg 1938, 2013)
    Karmakar, Rajdip
    Mamidipalli, Phani
    Yun, Sang Young
    Lee, Daesung
    ORGANIC LETTERS, 2014, 16 (03) : 1032 - 1032
  • [35] Solid-State Alder-Ene Reaction of 1-Hexene under High Pressure
    Xu, Jingqin
    Lang, Puyi
    Liang, Shijie
    Zhang, Jie
    Fei, Yunfan
    Wang, Yajie
    Gao, Dexiang
    Hattori, Takanori
    Abe, Jun
    Dong, Xiao
    Zheng, Haiyan
    Li, Kuo
    JOURNAL OF PHYSICAL CHEMISTRY LETTERS, 2025, 16 (10): : 2445 - 2451
  • [36] Benzannulation of Triynes Initiated by an Alder-Ene Reaction and Subsequent Trifluoromethylthiolate Addition
    Karmakar, Rajdip
    Mamidipalli, Phani
    Salzman, Ryan M.
    Hong, Seongwon
    Yun, Sang Young
    Guo, Wei
    Xia, Yuanzhi
    Lee, Daesung
    ORGANIC LETTERS, 2016, 18 (15) : 3530 - 3533
  • [37] The Palladium-Catalyzed Intramolecular Alder-Ene Reactions of O- and N-Linked 1,6-Enynes Incorporating Triethylsilyl Capping Groups
    Nugent, Jeremy
    Matousova, Eliska
    Banwell, Martin G.
    Willis, Anthony C.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23): : 12569 - 12589
  • [38] Aryne-mediated intramolecular Alder-ene reaction to form benzocyclobutenes
    Gupta, Saswata
    Lee, Daesung
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [39] Computational Study on Mechanisms and Origins of Selectivities in Rh(I)-Catalyzed Cycloisomerizations of 1,6-Allenynes with Tethered Unsaturated Carbon-Carbon Bonds
    Lu, Qianqian
    Gu, Jun
    Liu, Fang
    Li, Chunsen
    ACS CATALYSIS, 2021, 11 (08): : 4770 - 4783
  • [40] Rhodium(I) catalyzed allenic Alder-ene reaction: Scope and limitations.
    Brummond, KM
    McCabe, J
    Sill, PC
    Chen, HF
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U186 - U186
12345