Inter- and intramolecular enantioselective carbolithiation reactions

Asier Gómez-SanJuan, Nuria Sotomayor and Esther Lete
Beilstein J. Org. Chem. 2013, 9, 313–322. https://doi.org/10.3762/bjoc.9.36

Cite the Following Article

Inter- and intramolecular enantioselective carbolithiation reactions
Asier Gómez-SanJuan, Nuria Sotomayor and Esther Lete
Beilstein J. Org. Chem. 2013, 9, 313–322. https://doi.org/10.3762/bjoc.9.36

How to Cite

Gómez-SanJuan, A.; Sotomayor, N.; Lete, E. Beilstein J. Org. Chem. 2013, 9, 313–322. doi:10.3762/bjoc.9.36

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

  • Kacprzak, K.; Wojaczyńska, E.; Trochimczuk, A.; Steppeler, F.; Wojaczyński, J. doi:10.1002/9783527834204.ch10
  • Semba, K. Olefin Difunctionalization With Two Different Atoms; 1,2-Carbofunctionalization of Olefins With Heteroatoms Other than O and N. Reference Module in Chemistry, Molecular Sciences and Chemical Engineering; Elsevier, 2022. doi:10.1016/b978-0-32-390644-9.00017-2
  • Cigan, E.; Eggbauer, B.; Schrittwieser, J. H.; Kroutil, W. The role of biocatalysis in the asymmetric synthesis of alkaloids – an update. RSC advances 2021, 11, 28223–28270. doi:10.1039/d1ra04181a
  • Augros, D.; Comoy, C.; Fort, Y.; Leroux, F. R.; Panossian, A. The Winding Road towards an Atropo-enantioselective ‘ARYNE Coupling’. European Journal of Organic Chemistry 2021, 2021, 1971–1978. doi:10.1002/ejoc.202100087
  • Mandigma, M. J. P.; Domański, M.; Barham, J. P. C-Alkylation of alkali metal carbanions with olefins. Organic & biomolecular chemistry 2020, 18, 7697–7723. doi:10.1039/d0ob01180k
  • Marsico, G.; Scafato, P.; Belviso, S.; Superchi, S. Regio- and stereoselective intermolecular carbolithiation reactions. RSC advances 2020, 10, 32581–32601. doi:10.1039/d0ra06101h
  • Carral-Menoyo, A.; Sotomayor, N.; Lete, E. Palladium-catalysed Heck-type alkenylation reactions in the synthesis of quinolines. Mechanistic insights and recent applications. Catalysis Science & Technology 2020, 10, 5345–5361. doi:10.1039/d0cy00789g
  • Guyon, H.; Castanet, A.-S.; Boussonnière, A. Computational Insight into 1,2-Diamine, -Diether, and -Amino Ether Chiral Ligand-Mediated Carbolithiation: A Case of Enantioinduction Reversal. The Journal of organic chemistry 2020, 85, 8933–8943. doi:10.1021/acs.joc.0c00832
  • Alazet, S.; West, M. S.; Patel, P.; Rousseaux, S. A. L. Synthesis of Nitrile‐Bearing Quaternary Centers by an Equilibrium‐Driven Transnitrilation and Anion‐Relay Strategy. Angewandte Chemie 2019, 131, 10406–10410. doi:10.1002/ange.201903215
  • Alazet, S.; West, M. S.; Patel, P.; Rousseaux, S. A. L. Synthesis of Nitrile‐Bearing Quaternary Centers by an Equilibrium‐Driven Transnitrilation and Anion‐Relay Strategy. Angewandte Chemie (International ed. in English) 2019, 58, 10300–10304. doi:10.1002/anie.201903215
  • Liu, S.; Gray, D. L.; Zhu, L.; Girolami, G. S. Lithium–Olefin π-Complexes and the Mechanism of Carbolithiation: Synthesis, Solution Behavior, and Crystal Structure of (2,2-Dimethylpent-4-en-1-yl)lithium. Organometallics 2019, 38, 2199–2210. doi:10.1021/acs.organomet.9b00169
  • Simon, M.; Karaghiosoff, K.; Knochel, P. Diastereoselective Intramolecular Carbolithiations of Stereodefined Secondary Alkyllithiums Bearing a Remote Alkynylsilane. Organic letters 2018, 20, 3518–3521. doi:10.1021/acs.orglett.8b01290
  • Azcargorta, A. R.; Coya, E.; Panaite, A. M.; Sotomayor, N.; Lete, E. Intramolecular Addition of Heteroaryllithium Compounds onto Activated Alkenes: Access to Heterofused Indolizines and Pyrroloazepines. European Journal of Organic Chemistry 2017, 2017, 2462–2468. doi:10.1002/ejoc.201700123
  • Guyon, H.; Boussonnière, A.; Castanet, A.-S. Readily Accessible 1,2-Amino Ether Ligands for Enantioselective Intramolecular Carbolithiation. The Journal of organic chemistry 2017, 82, 4949–4957. doi:10.1021/acs.joc.7b00423
  • Ahmed, M.; Naseer, M. M. Organolithium-mediated cyclization reactions: a practical way to access hetero- and carbocycles. New Journal of Chemistry 2017, 41, 7824–7835. doi:10.1039/c7nj01763d
  • Gómez-SanJuan, A.; Arrasate, S.; González-Díaz, H.; Sotomayor, N.; Lete, E. Perturbation Theory Modeling of Intramolecular Carbolithiation Reactions. In Proceedings of MOL2NET, International Conference on Multidisciplinary Sciences, MDPI, 2015. doi:10.3390/mol2net-1-a013
  • Dawaigher, S.; Månsson, K.; Ascic, E.; Artacho, J.; Mårtensson, R.; Loganathan, N.; Wendt, O. F.; Harmata, M.; Snieckus, V.; Wärnmark, K. A Protocol for the exo-Mono and exo,exo-Bis Functionalization of the Diazocine Ring of Tröger’s Base. The Journal of organic chemistry 2015, 80, 12006–12014. doi:10.1021/acs.joc.5b01921
  • Mattalia, J.-M.; Nava, P. A Computational Study of the Intramolec­ular Carbolithiation of Aryllithiums: Solvent and Substituent Effects. European Journal of Organic Chemistry 2015, 2016, 394–401. doi:10.1002/ejoc.201501208
  • Doulcet, J.; Stephenson, G. R. The Use of (−)‐Sparteine/Organolithium Reagents for the Enantioselective Lithiation of 7,8‐Dipropyltetrathia[7]helicene: Single and Double Kinetic Resolution Procedures. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 18677–18689. doi:10.1002/chem.201502958
  • Egami, H.; Usui, Y.; Kawamura, S.; Shimizu, R.; Nagashima, S.; Sodeoka, M. Mechanistic study on a unique SN2′-type reaction of allylic alcohols with organolithium reagent accelerated by a proximal trifluoromethyl group. Journal of Fluorine Chemistry 2015, 179, 121–128. doi:10.1016/j.jfluchem.2015.07.024
Other Beilstein-Institut Open Science Activities