Synthesis of Enantioenriched α-Chiral Bicyclo[1.1.1]pentanes

被引:42
|
作者
Wong, Marie L. J. [1 ]
Mousseau, James J. [2 ]
Mansfield, Steven J. [1 ]
Anderson, Edward A. [1 ]
机构
[1] Univ Oxford, Chem Res Lab, 12 Mansfield Rd, Oxford OX1 3TA, England
[2] Pfizer Worldwide Res & Dev, Eastern Point Rd, Groton, CT 06340 USA
基金
英国工程与自然科学研究理事会;
关键词
BIOLOGICAL EVALUATION; BRIDGEHEAD; DESIGN; DERIVATIVES; FLUORINE; POTENT; SCOPE;
D O I
10.1021/acs.orglett.9b00691
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficient route to alpha-chiral BCPs, via highly diastereoselective asymmetric enolate functionalization. We also describe the application of this chemistry to the synthesis of BCP analogues of phenylglycine and tarenflurbil, the single enantiomer of the NSAID flurbiprofen.
引用
收藏
页码:2408 / 2411
页数:4
相关论文
共 50 条
  • [31] Automated Nanomole-Scale Reaction Screening toward Benzoate Bioisosteres: A Photocatalyzed Approach to Highly Elaborated Bicyclo[1.1.1]Pentanes
    Mousseau, James J.
    Perry, Matthew A.
    Bundesmann, Mark W.
    Chinigo, Gary M.
    Choi, Chulho
    Gallego, Gary
    Hicklin, Robert W.
    Hoy, Susan
    Limburg, David C.
    Sach, Neal W.
    Zhang, Yuan
    ACS CATALYSIS, 2022, 12 (01) : 600 - 606
  • [32] Recent Advances in the Synthetic Chemistry of Bicyclo[1.1.1]pentane
    Kanazawa, Junichiro
    Uchiyama, Masanobu
    SYNLETT, 2019, 30 (01) : 1 - 11
  • [33] A radical exchange process: synthesis of bicyclo[1.1.1]pentane derivatives of xanthates
    Rout, Saroj Kumar
    Marghem, Gilles
    Lan, Junjie
    Leyssens, Tom
    Riant, Olivier
    CHEMICAL COMMUNICATIONS, 2019, 55 (99) : 14976 - 14979
  • [34] Scalable Synthesis of 1-Bicyclo[1.1.1]pentylamine via a Hydrohydrazination Reaction
    Bunker, Kevin D.
    Sach, Neal W.
    Huang, Qinhua
    Richardson, Paul F.
    ORGANIC LETTERS, 2011, 13 (17) : 4746 - 4748
  • [35] Synthesis of C3-halo substituted bicyclo[1.1.1]pentylamines via halosulfoamidation of [1.1.1]propellane with sodium hypohalites and sulfonamides
    Li, Zhi
    Lan, Deyou
    Zhou, Wei
    Li, Jiacheng
    Zhu, Hui
    Yu, Chuanming
    Jiang, Xinpeng
    CHEMICAL COMMUNICATIONS, 2023, 59 (40) : 6056 - 6059
  • [36] Synthesis of a Bicyclo[1.1.1]pentane-Containing Aromatic Lipoxin B4 Analogue and Heteroaromatic Congeners
    Owen, Benjamin
    Guiry, Patrick J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (23)
  • [37] α-Cyclodextrin Encapsulation of Bicyclo[1.1.1]pentane Derivatives: a Storable Feedstock for Preparation of [1.1.1]Propellane
    Matsunaga, Tadafumi
    Kanazawa, Junichiro
    Ichikawa, Tomohiro
    Harada, Mei
    Nishiyama, Yusuke
    Duong, Nghia Tuan
    Matsumoto, Takashi
    Miyamoto, Kazunori
    Uchiyama, Masanobu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (05) : 2578 - 2582
  • [38] Exceptional reactivity of the bridgehead amine on bicyclo[1.1.1]pentane
    Lu, Yong
    Chen, Chuo
    ARKIVOC, 2023,
  • [39] Access to 2,2-Halofluorobicyclo[1.1.1] Pentanes via Non Ozone-Depleting Ethyl Dihalofluoroacetate
    Zhu, Ziyue
    Tang, Jiaqi
    Coe, Matthew
    Knieb, Alexander
    Xu, Yijie
    Lin, Daniel
    Zhang, Chao
    Prakash, G. K. Surya
    ADVANCED SYNTHESIS & CATALYSIS, 2025,
  • [40] Highly Functional Allyl-Bicyclo[1.1.1]pentane Synthesis by Radical-Initiated Three-Component Stereoselective Allylation
    Zeng, Qian
    Shi, Wangyu
    Kleij, Arjan W.
    JACS AU, 2025, 5 (02): : 913 - 921