Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides

Yury Minko, Morgane Pasco, Helena Chechik and Ilan Marek
Beilstein J. Org. Chem. 2013, 9, 526–532. https://doi.org/10.3762/bjoc.9.57

Supporting Information

Supporting Information File 1: Full experimental procedures and detailed analytical data for the synthesis of all new compounds.
Format: PDF Size: 582.4 KB Download

Cite the Following Article

Regio- and stereoselective carbometallation reactions of N-alkynylamides and sulfonamides
Yury Minko, Morgane Pasco, Helena Chechik and Ilan Marek
Beilstein J. Org. Chem. 2013, 9, 526–532. https://doi.org/10.3762/bjoc.9.57

How to Cite

Minko, Y.; Pasco, M.; Chechik, H.; Marek, I. Beilstein J. Org. Chem. 2013, 9, 526–532. doi:10.3762/bjoc.9.57

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.

Citations to This Article

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

Scholarly Works

  • Takimoto, M.; Hou, Z. Regioselective Carbozincation and Further Functionalization of Allenamides Catalyzed by an N‐Heterocyclic Carbene (NHC)‐Copper Complex. Asian Journal of Organic Chemistry 2023, 12. doi:10.1002/ajoc.202300372
  • Xiao, Y.; Tang, L.; Xu, T.-T.; Sheng, J.-Y.-H.; Zhou, Z.; Yue, L.; Wang, G.; Oestreich, M.; Feng, J.-J. Atom-economic and stereoselective catalytic synthesis of fully substituted enol esters/carbonates of amides in acyclic systems enabled by boron Lewis acid catalysis. Chemical science 2023, 14, 5608–5618. doi:10.1039/d3sc01394d
  • Dian, L.; Marek, I. doi:10.1002/9783527830237.ch7
  • Xiao, Y.; Tang, L.; Xu, T.-T.; Feng, J.-J. Boron Lewis Acid Catalyzed Intermolecular trans-Hydroarylation of Ynamides with Hydroxyarenes. Organic letters 2022, 24, 2619–2624. doi:10.1021/acs.orglett.2c00574
  • Chai, J.; Ding, W.; Wang, C.; Ito, S.; Wu, J.; Yoshikai, N. Ritter-type iodo( iii )amidation of unactivated alkynes for the stereoselective synthesis of multisubstituted enamides. Chemical science 2021, 12, 15128–15133. doi:10.1039/d1sc05240c
  • Golling, S.; Leroux, F. R.; Donnard, M. Versatile Access to Tetrasubstituted 2-Amidoacroleins through Formal Silylformylation of Ynamides. Organic letters 2021, 23, 8093–8097. doi:10.1021/acs.orglett.1c03141
  • Corpas, J.; Mauleón, P.; Arrayás, R. G.; Carretero, J. C. Transition-Metal-Catalyzed Functionalization of Alkynes with Organoboron Reagents: New Trends, Mechanistic Insights, and Applications. ACS Catalysis 2021, 11, 7513–7551. doi:10.1021/acscatal.1c01421
  • Hu, X.; Xie, X.; Gan, Y.; Wang, G.; Liu, Y. Nickel-Catalyzed β-Regioselective Amination/Cyclization of Ynamide-Nitriles with Amines: Synthesis of Functionalized 3-Aminoindoles and 4-Aminoisoquinolines. Organic letters 2021, 23, 1296–1301. doi:10.1021/acs.orglett.0c04278
  • Lynch, C. C.; Sripada, A.; Wolf, C. Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications. Chemical Society reviews 2020, 49, 8543–8583. doi:10.1039/d0cs00769b
  • Kang, K.; Sakamoto, K.; Nishimoto, Y.; Yasuda, M. Synthesis of (Z)-β-(Carbonylamino)alkenylindium through Regioselective anti-Carboindation of Ynamides and Its Transformation to Multisubstituted Enamides. Chemistry (Weinheim an der Bergstrasse, Germany) 2020, 26, 4930–4934. doi:10.1002/chem.201905175
  • Huang, J.; Marek, I. Construction of Acyclic Vicinal Tertiary and Quaternary Carbon Stereocenters via a Pd‐Catalyzed Allylic Alkylation of Stereodefined Polysubstituted Ketene Aminals. European Journal of Organic Chemistry 2020, 2020, 3133–3137. doi:10.1002/ejoc.201901741
  • Wagner, P.; Donnard, M.; Girard, N. Ligand-Controlled Regiodivergent Hydroformylation of Ynamides: A Stereospecific and Regioselective Access to 2- and 3-Aminoacroleins. Organic letters 2019, 21, 8861–8866. doi:10.1021/acs.orglett.9b03566
  • Wang, P.-Y.; Duret, G.; Marek, I. Regio- and Stereoselective Synthesis of Fully Substituted Silyl Enol Ethers of Ketones and Aldehydes in Acyclic Systems. Angewandte Chemie (International ed. in English) 2019, 58, 14995–14999. doi:10.1002/anie.201909089
  • Wang, P.; Duret, G.; Marek, I. Regio‐ and Stereoselective Synthesis of Fully Substituted Silyl Enol Ethers of Ketones and Aldehydes in Acyclic Systems. Angewandte Chemie 2019, 131, 15137–15141. doi:10.1002/ange.201909089
  • Volpe, R.; Lepage, R. J.; White, J. M.; Krenske, E. H.; Flynn, B. L. Asymmetric synthesis of multiple quaternary stereocentre-containing cyclopentyls by oxazolidinone-promoted Nazarov cyclizations. Chemical science 2018, 9, 4644–4649. doi:10.1039/c8sc00031j
  • Bang, J.; Oh, C.; Lee, E.; Jeong, H.; Lee, J.; Ryu, J. Y.; Kim, J.; Yu, C.-M. A Regulation of Regiodivergent Routes for Enantioselective Aldol Addition of 2-Alkyl Allenoates with Aldehydes: α-Addition versus γ-Addition. Organic letters 2018, 20, 1521–1525. doi:10.1021/acs.orglett.8b00219
  • Huang, J. Q.; Nairoukh, Z.; Marek, I. Electrophilic Oxidation of Stereodefined Polysubstituted Silyl Ketone Aminals. European Journal of Organic Chemistry 2017, 2018, 614–618. doi:10.1002/ejoc.201701516
  • Baldassari, L. L.; de la Torre, A.; Li, J.; Lüdtke, D. S.; Maulide, N. Ynamide Preactivation Allows a Regio- and Stereoselective Synthesis of α,β-Disubstituted Enamides. Angewandte Chemie (International ed. in English) 2017, 56, 15723–15727. doi:10.1002/anie.201709128
  • Baldassari, L. L.; de la Torre, A.; Li, J.; Lüdtke, D. S.; Maulide, N. Regio- und stereoselektive Synthese α,β-disubstituierter Enamide durch Voraktivierung von Inamiden. Angewandte Chemie 2017, 129, 15929–15933. doi:10.1002/ange.201709128
  • Starkov, P.; Moore, J. T.; Duquette, D. C.; Stoltz, B. M.; Marek, I. Enantioselective Construction of Acyclic Quaternary Carbon Stereocenters: Palladium-Catalyzed Decarboxylative Allylic Alkylation of Fully Substituted Amide Enolates. Journal of the American Chemical Society 2017, 139, 9615–9620. doi:10.1021/jacs.7b04086
Other Beilstein-Institut Open Science Activities