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
  • [41] Rhodium-Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3-Diketones
    Hilpert, Lukas J.
    Breit, Bernhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (29) : 9939 - 9943
  • [42] Rhodium-catalyzed regio- and stereoselective codimerization of alkenes and electron-deficient internal alkynes leading to 1,3-dienes
    Shibata, Yu
    Hirano, Masao
    Tanaka, Ken
    ORGANIC LETTERS, 2008, 10 (13) : 2829 - 2831
  • [43] Rhodium-Catalyzed Enantioselective Formal [4+1] Cyclization of Benzyl Alcohols and Benzaldimines: Facile Access to Silicon-Stereogenic Heterocycles
    Shen, Bingxue
    Pan, Deng
    Xie, Wanying
    Li, Xiao-Xi
    Yu, Songjie
    Huang, Genping
    Li, Xingwei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (01)
  • [44] Efficient Rhodium-Catalyzed Conjugate Addition of Arylboronic Acids to Unsaturated Furano Esters for the Highly Stereoselective Synthesis of Four Natural Trisubstituted Furanolignans
    Mondiere, Aurelie
    Pousse, Guillaume
    Bouyssi, Didier
    Balme, Genevieve
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (25) : 4225 - 4229
  • [45] Highly Stereoselective Synthesis of Tetrasubstituted Vinyl Selenides via Rhodium-Catalyzed [1,4]-Acyl Migration of Selenoesters and Diazo Compounds
    Liu, Xun-Shen
    Li, Mingjia
    Dong, Kexin
    Peng, Shaoting
    Liu, Lu
    ORGANIC LETTERS, 2022, 24 (11) : 2175 - 2180
  • [46] Rhodium-catalyzed C-H activation/cyclization of aryl sulfoximines with iodonium ylides towards polycyclic 1,2-benzothiazines
    Huang, Gao
    Shan, Yujia
    Yu, Jin-Tao
    Pan, Changduo
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (46) : 10085 - 10089
  • [47] ReI-Catalyzed highly regio- and stereoselective C-H addition to terminal and internal alkynes
    Chang, Yu-Che
    Prakash, Sekar
    Cheng, Chien-Hong
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (04): : 432 - 436
  • [48] Pd(0)-catalyzed atom transfer radical cyclization of N-allyl-α-chloroamides: highly stereoselective synthesis of substituted γ-lactam
    Liu, Qiang
    Chen, Chen
    Tong, Xiaofeng
    TETRAHEDRON LETTERS, 2015, 56 (30) : 4483 - 4485
  • [49] Highly stereoselective heterogeneous palladium-catalyzed transfer semihydrogenation of internal alkynes to access cis-alkenes
    Huang, Wencheng
    Li, Jianying
    Chen, Qiurong
    Cai, Mingzhong
    JOURNAL OF CHEMICAL RESEARCH, 2019, 43 (5-6) : 189 - 195
  • [50] Efficient Access to Isoquinolines via Rhodium-Catalyzed Oxidative Annulation of Pyridyl C-H Bonds Directed by Carbonyl with Internal Alkynes
    Shi, Lijun
    Wen, Mingshan
    Li, Fuwei
    SYNTHESIS-STUTTGART, 2021, 53 (03): : 538 - 546
12345