Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene

Frederick J. Seidl and Noah Z. Burns
Beilstein J. Org. Chem. 2016, 12, 1361–1365. https://doi.org/10.3762/bjoc.12.129

Supporting Information

Supporting Information File 1: Experimental procedures, full characterization of new compounds, and spectral data.
Format: PDF Size: 1.2 MB Download

Cite the Following Article

Selective bromochlorination of a homoallylic alcohol for the total synthesis of (−)-anverene
Frederick J. Seidl and Noah Z. Burns
Beilstein J. Org. Chem. 2016, 12, 1361–1365. https://doi.org/10.3762/bjoc.12.129

How to Cite

Seidl, F. J.; Burns, N. Z. Beilstein J. Org. Chem. 2016, 12, 1361–1365. doi:10.3762/bjoc.12.129

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 119.0 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Zhang, D.; Pu, M.; Liu, Z.; Zhou, Y.; Yang, Z.; Liu, X.; Wu, Y.-D.; Feng, X. Enantioselective anti-Dihalogenation of Electron-Deficient Olefin: A Triplet Halo-Radical Pylon Intermediate. Journal of the American Chemical Society 2023, 145, 4808–4818. doi:10.1021/jacs.2c13810
  • Lubaev, A. E.; Rathnayake, M. D.; Eze, F.; Bayeh-Romero, L. Catalytic Chemo-, Regio-, Diastereo-, and Enantioselective Bromochlorination of Unsaturated Systems Enabled by Lewis Base-Controlled Chloride Release. Journal of the American Chemical Society 2022, 144, 13294–13301. doi:10.1021/jacs.2c04588
  • Strehl, J.; Fastie, C.; Hilt, G. The Electrochemical cis-Chlorination of Alkenes. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 17341–17345. doi:10.1002/chem.202103316
  • Cheng, J.; Li, Y.-H.; Huang, J.; Yang, Z. Total Syntheses of Vicinal Dichloride Monoterpenes Enabled by Aza-Belluš-Claisen Rearrangement. Organic letters 2021, 23, 8465–8470. doi:10.1021/acs.orglett.1c03187
  • Ju, W.; Wang, X.; Tian, H.; Gui, J. Asymmetric Total Synthesis of Clionastatins A and B. Journal of the American Chemical Society 2021, 143, 13016–13021. doi:10.1021/jacs.1c07511
  • Ashtekar, K. D.; Jaganathan, A.; Borhan, B.; Whitehead, D. C. Organic Reactions - Enantioselective Halofunctionalization of Alkenes. Organic Reactions 2021, 1–266. doi:10.1002/0471264180.or105.01
  • Bock, J.; Guria, S.; Wedek, V.; Hennecke, U. Enantioselective Dihalogenation of Alkenes. Chemistry (Weinheim an der Bergstrasse, Germany) 2021, 27, 4517–4530. doi:10.1002/chem.202003176
  • Lian, P.; Long, W.; Li, J.; Zheng, Y.; Wan, X. Visible‐Light‐Induced Vicinal Dichlorination of Alkenes through LMCT Excitation of CuCl2. Angewandte Chemie 2020, 132, 23809–23814. doi:10.1002/ange.202010801
  • Pengcheng, L.; Long, W.; Jingjing, L.; Zheng, Y.; Wan, X. Visible‑Light‑Induced Vicinal Dichlorination of Alkenes through LMCT Excitation of CuCl 2. Angewandte Chemie (International ed. in English) 2020, 59, 23603–23608. doi:10.1002/anie.202010801
  • Wedek, V.; Van Lommel, R.; Daniliuc, C. G.; De Proft, F.; Hennecke, U. Organokatalytische, enantioselektive Dichlorierung unfunktionalisierter Alkene. Angewandte Chemie 2019, 131, 9339–9343. doi:10.1002/ange.201901777
  • Wedek, V.; Van Lommel, R.; Daniliuc, C. G.; De Proft, F.; Hennecke, U. Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes. Angewandte Chemie (International ed. in English) 2019, 58, 9239–9243. doi:10.1002/anie.201901777
  • Seidl, F. J.; Min, C.; Lopez, J. A.; Burns, N. Z. Catalytic Regio- and Enantioselective Haloazidation of Allylic Alcohols. Journal of the American Chemical Society 2018, 140, 15646–15650. doi:10.1021/jacs.8b10799
  • Landry, M. L.; Burns, N. Z. Catalytic Enantioselective Dihalogenation in Total Synthesis. Accounts of chemical research 2018, 51, 1260–1271. doi:10.1021/acs.accounts.8b00064
  • Bhadra, S.; Yamamoto, H. Substrate Directed Asymmetric Reactions. Chemical reviews 2018, 118, 3391–3446. doi:10.1021/acs.chemrev.7b00514
  • Blunt, J. W.; Carroll, A. R.; Copp, B. R.; Davis, R. A.; Keyzers, R. A.; Prinsep, M. R. Marine natural products. Natural product reports 2018, 35, 8–53. doi:10.1039/c7np00052a
  • Thiel, N. O.; Teichert, J. F. Interhalogenierung: Problemkind der Alkenbromierung. Nachrichten aus der Chemie 2017, 65, 772–775. doi:10.1002/nadc.20174065093

Patents

  • YANG ZHEN; CHENG JIANGQUN; HUANG JUN; GONG JIANXIAN; ZHANG WEIBIN. Compound containing halogen atom chiral center, preparation method and application of compound, and preparation method of natural product containing halogen atom chiral center. CN 112321536 A, Feb 5, 2021.
Other Beilstein-Institut Open Science Activities