Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

被引：0
|
作者：
Schmidt, Johannes P. [1 ]
Breit, Bernhard [1 ]
机构：
[1] Institute for Organic Chemistry, Albert-Ludwigs-Universität Freiburg, Albertstraße 21, Freiburg im Breisgau,79104, Germany
来源：
Advanced Materials | 2020年 / 59卷 / 52期
关键词：
Stereoselectivity;
D O I：
10.1002/ANGE.202009166
中图分类号：
学科分类号：
摘要：
A comprehensive study of a diastereoselective Rhcatalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (—)-centrolobine. © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码：23691 / 23696
相关论文
共 50 条
  • [31] Completely OH-Selective FeCl3-Catalyzed Prins Cyclization: Highly Stereoselective Synthesis of 4-OH-Tetrahydropyrans
    Zheng, Ke
    Liu, Xiaohua
    Qin, Song
    Xie, Mingsheng
    Lin, Lili
    Hu, Changwei
    Feng, Xiaoming
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (42) : 17564 - 17573
  • [32] Highly Enantioselective Rhodium-Catalyzed Cross-Addition of Silylacetylenes to Cyclohexadienone-Tethered Internal Alkynes
    Duan, Chang-Lin
    Tan, Yun-Xuan
    Zhang, Jun-Li
    Yang, Shiping
    Dong, Han-Qing
    Tian, Ping
    Lin, Guo-Qiang
    ORGANIC LETTERS, 2019, 21 (06) : 1690 - 1693
  • [33] Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles
    Hilpert, Lukas J.
    Sieger, Simon V.
    Haydl, Alexander M.
    Breit, Bernhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (11) : 3378 - 3381
  • [34] Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes towards Chiral Allylated Triazoles and Tetrazoles
    Sieger, Simon, V
    Lubins, Ilja
    Breit, Bernhard
    CATALYSTS, 2022, 12 (10)
  • [35] Stereoselective synthesis 3-alkylideneoxindoles by rhodium-catalyzed cyclization reaction of 2-alkynylaryl isocyanates with aryl- and alkenylboronic acids
    Miura, Tomoya
    Takahashi, Yusuke
    Murakami, Masahiro
    ORGANIC LETTERS, 2007, 9 (24) : 5075 - 5077
  • [36] Rhodium-Catalyzed, Phosphorus(III)-Directed Hydroarylation of Internal Alkynes: Facile and Efficient Access to New Phosphine Ligands
    Luo, Huanhuan
    Wang, Dawei
    Wang, Minyan
    Shi, Zhuangzhi
    SYNLETT, 2022, 33 (04) : 351 - 356
  • [37] Rhodium-Catalyzed Asymmetric Tandem Cyclization for Efficient and Rapid Access to Underexplored Heterocyclic Tertiary Allylic Alcohols Containing a Tetrasubstituted Olefin
    Li, Yi
    Xu, Ming-Hua
    ORGANIC LETTERS, 2014, 16 (10) : 2712 - 2715
  • [38] Chiral Pincer Carbodicarbene Ligands for Enantioselective Rhodium-Catalyzed Hydroarylation of Terminal and Internal 1,3-Dienes with Indoles
    Marcum, Justin S.
    Roberts, Courtney C.
    Manan, Rajith S.
    Cervarich, Tia N.
    Meek, Simon J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (44) : 15580 - 15583
  • [39] Rhodium-catalyzed hydrophosphorylation of terminal alkynes leading to highly selective formation of (E)-alkenylphosphonates:: Complete reversal of regioselectivity to the palladium-catalyzed counterpart
    Zhao, CQ
    Han, LB
    Goto, M
    Tanaka, M
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2001, 40 (10) : 1929 - 1932
  • [40] Rhodium-Catalyzed Highly Regio- and Enantioselective Hydrogenation of Tetrasubstituted Allenyl Sulfones: An Efficient Access to Chiral Allylic Sulfones
    Long, Jiao
    Shi, Liyang
    Li, Xiong
    Lv, Hui
    Zhang, Xumu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13248 - 13251
12345