Expedient Synthesis of Chiral Oxazolidinone Scaffolds via Rhodium-Catalyzed Asymmetric Ring-Opening with Sodium Cyanate

被引：60
|
作者：
Tsui, Gavin Chit [1 ]
Ninnemann, Nina M. [1 ]
Hosotani, Akihito [1 ]
Lautens, Mark [1 ]
机构：
[1] Univ Toronto, Dept Chem, Davenport Res Labs, Toronto, ON M5S 3H6, Canada
来源：
ORGANIC LETTERS | 2013年 / 15卷 / 05期
基金：
日本学术振兴会; 加拿大自然科学与工程研究理事会;
关键词：
OXABICYCLIC ALKENES; ARYL; ACIDS;
D O I：
10.1021/ol4000668
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A method for synthesizing chiral oxazolidinone scaffolds from readily available oxabicyclic alkenes is described. The reaction utilizes a domino sequence of Rh(I)-catalyzed asymmetric ring-opening (ARO) with sodium cyanate as a novel nucleophile followed by intramolecular cyclization to generate oxazolidinone products in excellent enantioselectivities (trans stereochemistry).
引用
收藏
页码：1064 / 1067
页数：4
相关论文
共 18 条
  • [1] Rhodium-Catalyzed Asymmetric Arylative Ring-Opening Reactions of Heterobicyclic Alkenes with Anilines
    Chen, Jingchao
    Zou, Lingling
    Zeng, Chaoyuan
    Zhou, Yongyun
    Fan, Baomin
    ORGANIC LETTERS, 2018, 20 (05) : 1283 - 1286
  • [2] Enantioselective Synthesis of Chiral Ferrocenyl Aminoalcohols: Simultaneous Induction of Multiple Types of Chirality by a Rhodium-Catalyzed Asymmetric Ring-Opening Strategy
    Isoda, Takamu
    Jimba, Komei
    Kawashima, Kyohei
    Nishinoiri, Takahiro
    Mori, Seiji
    Tsurusaki, Akihiro
    Kamikawa, Ken
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025,
  • [3] Tunable chiral monophosphines as ligands in enantioselective rhodium-catalyzed ring-opening of oxabenzonorbornadienes with amines
    Luo, Renshi
    Xie, Ling
    Liao, Jianhua
    Xin, Hu
    Chan, Albert S. C.
    TETRAHEDRON-ASYMMETRY, 2014, 25 (09) : 709 - 717
  • [4] Exploiting Distal Reactivity of Coumarins: A Rhodium-Catalyzed Vinylogous Asymmetric Ring-Opening Reaction
    Loh, Charles C. J.
    Schmid, Matthias
    Peters, Brendan
    Fang, Xiang
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (14) : 4600 - 4604
  • [5] Highly Efficient Rhodium-Catalyzed Asymmetric Ring-Opening Reactions of Oxabenzonorbornadiene with Amine Nucleophiles
    Long, Yuhua
    Zhao, Shuangqi
    Zeng, Heping
    Yang, Dingqiao
    CATALYSIS LETTERS, 2010, 138 (1-2) : 124 - 133
  • [6] Rhodium Catalyzed Asymmetric Ring-Opening Reaction of Oxabenzonorbornadienes with Anhydride
    Hu, Jirong
    Xu, Jianbin
    Zou, Lingling
    Lu, Haiping
    Fan, Ruifeng
    Liu, Na
    Zhou, Yongyun
    Fan, Baomin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2018, 38 (07) : 1687 - 1694
  • [7] Rhodium-catalyzed ring-opening reactions of heterobicyclic alkenes with heteroarene nucleophiles
    Neufeld, Eric
    Pounder, Austin
    Tam, William
    TETRAHEDRON LETTERS, 2023, 127
  • [8] Rhodium-catalyzed Asymmetric Ring-opening Reactions of N-Boc-azabenzonorbornadiene with N-Substituted Piperazine Nucleophiles
    Long Yuhua
    Yang Dingqiao
    Zeng Heping
    Xie Lei
    Wu Lihuan
    Mo Haihong
    Zuo Xiongjun
    CHINESE JOURNAL OF CHEMISTRY, 2010, 28 (02) : 235 - 242
  • [9] Rhodium-catalyzed asymmetric ring opening reaction of oxabenzonorbornadienes with amines using ZnI2 as the activator
    Xu, Xin
    Chen, Jingchao
    He, Zhenxiu
    Zhou, Yongyun
    Fan, Baomin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (08) : 2480 - 2486
  • [10] Synthesis of tetrasubstituted benzenes via rhodium(I)-catalysed ring-opening benzannulation of cyclobutenols with alkynes
    Matsuda, Takanori
    Miura, Norio
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (21) : 3424 - 3427
12