Nickel-Catalyzed Asymmetric Reductive [3+2] Annulation of o-Haloaromatic β-Alkenyl Ketones with Alkynes via Alkene Isomerization: Enantioselective Synthesis of 1-Alkenyl 1H-Inden-1-ols

被引：8
|
作者：
Han, Ya-Fei [1 ,2 ]
Li, Yang [2 ]
Ouyang, Xuan-Hui [2 ]
Hu, Ming [1 ,2 ]
Tan, Ze [1 ]
Li, Jin-Heng [1 ,2 ,3 ,4 ]
机构：
[1] Hunan Univ, State Key Lab Chemo Biosensing & Chemometr, Changsha 410082, Peoples R China
[2] Nanchang Hangkong Univ, Key Lab Jiangxi Prov Persistent Pollutants Contro, Nanchang 330063, Jiangxi, Peoples R China
[3] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[4] Henan Normal Univ, Sch Chem & Chem Engn, Kaifeng 475004, Henan, Peoples R China
来源：
ACS CATALYSIS | 2021年 / 11卷 / 16期
基金：
中国国家自然科学基金;
关键词：
nickel; asymmetric reductive [3+2] annulation; o-haloaromatic beta-alkenyl ketones; alkynes; 1H-inden-1-ols; REGIOSELECTIVE CARBOCYCLIZATION; EFFICIENT ROUTE; INDENOLS; ACIDS; CYCLOADDITION; BIOSYNTHESIS; ACCESS;
D O I：
10.1021/acscatal.1c02613
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A nickel-catalyzed asymmetric reductive [3 + 2] annulation of o-haloaromatic beta-alkenyl ketones with alkynes through alkyne dicarbofunctionalization and alkene isomerization cascades is disclosed, enabling the formation of highly enantiomerically enriched 1-alkenyl 1H-inden-1-ols that possess an important stereogenic quaternary carbon and an active alkene unit. This reaction shows notable features of a broad substrate scope and excellent controlled stereo-, chemo-, and regio-selectivity and is useful for synthetic applications to the construction of diverse chiral tertiary alcohol system-containing sterically demanding structures and their derivatized chiral building blocks.
引用
收藏
页码：10115 / 10122
页数：8
相关论文
共 30 条
  • [21] Rhodium-Catalyzed Spiro Indenyl Benzoxazine Synthesis via C-H Activation/Annulation of 3-Aryl-2H-Benzo[b][1,4]oxazines and Alkynes
    Tan, Heng
    Laishram, Ronibala Devi
    Zhang, Xuexin
    Shi, Guangrui
    Li, Kangkui
    Chen, Jingchao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (29) : 4542 - 4546
  • [22] Chemo- and Regioselective Synthesis of Functionalized 1H-imidazo[1,5-a]indol-3(2H)-ones via a Redox-Neutral Rhodium(III)-Catalyzed [4+1] Annulation between Indoles and Alkynes
    Zhao, Fei
    Chen, Jing
    Qiao, Jin
    Lu, Yangbin
    Zhang, Xiaoning
    Mao, Hui
    Lu, Shiyao
    Gong, Xin
    Liu, Siyu
    Wu, Xiaowei
    Dai, Long
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (18) : 4380 - 4389
  • [23] Copper-Catalyzed Asymmetric Reaction of Alkenyl Diynes with Styrenes by Formal [3+2] Cycloaddition via Cu-Containing AllCarbon 1,3-Dipoles: Access to Chiral Pyrrole-Fused Bridged [2.2.1] Skeletons
    Hong, Feng-Lin
    Chen, Yang-Bo
    Ye, Si-Han
    Zhu, Guang-Yu
    Zhu, Xin-Qi
    Lu, Xin
    Liu, Rai-Shung
    Ye, Long-Wu
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (16) : 7618 - 7626
  • [24] Cp*CoIII-Catalyzed Synthesis of Pyrido[2′,1′:2,3]pyrimido[1,6-a]indol-5-iums via Tandem C-H Activation and Subsequent Annulation from 1-(Pyridin-2-yI)-1H-indoles and Internal Alkynes
    Yang, Yuhan
    Li, Bo
    Liu, Wenmin
    Zhang, Rumeng
    Yu, Lintao
    Ma, Qin-Ge
    Lv, Rongrong
    Du, Donghua
    Li, Ting
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 11335 - 11345
  • [25] Enantioselective synthesis of 1,2,3,4-tetrahydroquinoline-4-ols and 2,3-dihydroquinolin-4(1H)-ones via a sequential asymmetric hydroxylation/diastereoselective oxidation process using Rhodococcus equi ZMU-LK19
    Li, Ke
    Wang, Juxiang
    Wu, Kailin
    Zheng, Daijun
    Zhou, Xiaojian
    Han, Wenyong
    Wan, Nanwei
    Cui, Baodong
    Chen, Yongzheng
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (17) : 3580 - 3584
  • [26] Phosphine-Catalyzed Asymmetric [4+2] Annulation of Vinyl Ketones with Oxindole-Derived α,β-Unsaturated Imines: Enantioselective Syntheses of 2′,3′-Dihydro-1′H-spiro[indoline-3,4′-pyridin]-2-ones
    Zhang, Xiao-Nan
    Chen, Gen-Qiang
    Dong, Xiang
    Wei, Yin
    Shi, Min
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (17) : 3351 - 3357
  • [27] A facile metal-free one-flask synthesis of multi-substituted furans via a BF3•Et2O mediated formal [4+1] reaction of 3-chloro-3-phenyldiazirines and α,β-alkenyl ketones
    Zhang, Zixin
    Huang, Aimin
    Ma, Lin
    Xu, Jian-hua
    Zhang, Min
    RSC ADVANCES, 2022, 12 (24) : 15190 - 15195
  • [28] Metal-Free Intramolecular [3+2] Cycloaddition of γ-Hydroxy Acetylenic Ketones with Alkynes for the Synthesis of Naphtho[1,2-c]furan-5-ones and Its Derivatization via a Selective C(sp2)-H Deuteration Reaction
    Ning, Si-Si
    Meng, Dan
    Zhang, Jie-Yun
    Liu, Shi-Lei
    Zhou, Ni-Ni
    Jin, Xiaojie
    Zhu, Hai-Tao
    JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (11): : 7347 - 7358
  • [29] Synthesis of Polysubstituted Furans Based on a Stepwise Sonogashira Coupling of (Z)-3-Iodoalk-2-en-1-ols with Terminal Propargylic Alcohols and Subsequent Au(I)- or Pd(II)-Catalyzed Cyclization-Aromatization via Elimination of H2O
    Zhang, Xiaobing
    Lu, Zhan
    Fu, Chunling
    Ma, Shengming
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (08): : 2589 - 2598
  • [30] Diastereoselective Synthesis of 2-Arylmethylene-6-hydroxyspiro[4.5]deca-7-ones via FeCl3•6H2O-Catalyzed Spiroannulation/Hydride Transfer of 6-(5-Arylpent-4-yn-1-yl)-7oxabicyclo[4.1.0]heptan-2-ols
    Lin, Hsin-Hui
    Lee, Kuan-Yi
    Chen, Yin-An
    Liu, Chi-Fan
    Yeh, Ming-Chang P.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (23): : 11802 - 11811
123