Zinc-Catalyzed Cyclopropenation of Alkynes via 2-Furylcarbenoids

被引：50
|
作者：
Gonzalez, Maria J.
Lopez, Luis A. [1 ]
Vicente, Ruben
机构：
[1] Univ Oviedo, Dept Quim Organ & Inorgan, E-33006 Oviedo, Spain
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 21期
关键词：
SOLID-STATE STRUCTURE; TERMINAL ALKYNES; CYCLOPROPANATION; INSERTION; FURAN; GENERATION; IZNCH2I;
D O I：
10.1021/ol502848n
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unprecedented cyclopropenation reaction of alkynes catalyzed by ZnCl2 is reported. While SimmonsSmith-type carbenoids failed in the [2 + 1]-cycloaddition with alkynes, the use of enynones as the carbene source enables the preparation of substituted 2-furyl cyclopropene derivatives with remarkable scope.
引用
收藏
页码：5780 / 5783
页数：4
相关论文
共 50 条
  • [21] Zinc-catalyzed enantioselective hydrosilylation of imines
    Park, Bu-Mahn
    Mun, Soungyun
    Yun, Jaesook
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (09) : 1029 - 1032
  • [22] Highly enantioselective rhodium-catalyzed cyclopropenation of terminal alkynes with styryldiazoacetates
    Briones, John F.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [23] Zinc-Catalyzed Allenylations of Aldehydes and Ketones
    Fandrick, Daniel R.
    Saha, Jaideep
    Fandrick, Keith R.
    Sanyal, Sanjit
    Ogikubo, Junichi
    Lee, Heewon
    Roschangar, Frank
    Song, Jinhua J.
    Senanayake, Chris H.
    ORGANIC LETTERS, 2011, 13 (20) : 5616 - 5619
  • [24] Alkynylboranes: A Practical Approach by Zinc-Catalyzed Dehydrogenative Coupling of Terminal Alkynes with 1,8-Naphthalenediaminatoborane
    Tsuchimoto, Teruhisa
    Utsugi, Hirokazu
    Sugiura, Tetsuya
    Horio, Shin
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (01) : 77 - 82
  • [25] Cooperative Gold/Zinc-catalyzed Cascade Approach to Tryptophan Derivatives from N-arylhydroxylamines and Alkynes
    Wang, Min
    Liu, Xiao
    Wang, Liying
    Lu, Haifeng
    Gao, Hongyin
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 11 (04)
  • [26] Zinc-catalyzed synthesis of 2-alkenylfurans via cross-coupling of enynones and diazo compounds
    Gonzalez, Jesus
    Lopez, Luis A.
    Vicente, Ruben
    CHEMICAL COMMUNICATIONS, 2014, 50 (62) : 8536 - 8538
  • [27] Mechanism and origin of enantioselectivity in the Rh2(OAc)(DPTI)3-catalyzed cyclopropenation of alkynes
    Nowlan, DT
    Singleton, DA
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (17) : 6190 - 6191
  • [28] Rh2(S-PTAD)4-catalyzed asymmetric cyclopropenation of aryl alkynes
    Briones, John F.
    Davies, Huw M. L.
    TETRAHEDRON, 2011, 67 (24) : 4313 - 4317
  • [29] Recent developments in enantioselective zinc-catalyzed transformations
    Pellissier, Helene
    COORDINATION CHEMISTRY REVIEWS, 2021, 439
  • [30] Mechanism and origin of enantioselectivity in the Rh2(OAc)(DPTI) 3-catalyzed cyclopropenation of alkynes
    1600, American Chemical Society, Columbus, United States (127):
12345