Gold(I)-catalyzed synthesis of γ-vinylbutyrolactones by intramolecular oxaallylic alkylation with alcohols

Scholarly Works

• Sankar, D. R.; Neetha, M.; Anilkumar, G. Gold-Catalyzed Lactone Synthesis: Advancements and Insights. Chemical record (New York, N.Y.) 2024, 24, e202400071. doi:10.1002/tcr.202400071
• Iazzetti, A.; Allevi, D.; Calcaterra, A.; Fabrizi, G.; Goggiamani, A.; Mazzoccanti, G.; Sferrazza, A.; Verdiglione, R.; Vergine, V. Highly Efficient and Mild Gold (I) Catalyzed Synthesis of 3,8-Diarylidene-2,7-dioxaspiro[4.4]nonane-1,6-diones. Molecules (Basel, Switzerland) 2022, 28, 300. doi:10.3390/molecules28010300
• Hur, J.; Jang, J.; Sim, J. A Review of the Pharmacological Activities and Recent Synthetic Advances of γ-Butyrolactones. International journal of molecular sciences 2021, 22, 2769. doi:10.3390/ijms22052769
• Müller, D. S.; Curbet, I.; Raoul, Y.; Le Nôtre, J.; Baslé, O.; Mauduit, M. Stereoretentive Olefin Metathesis Made Easy: In Situ Generation of Highly Selective Ruthenium Catalysts from Commercial Starting Materials. Organic letters 2018, 20, 6822–6826. doi:10.1021/acs.orglett.8b02943
• Liu, J.; Miotto, R. J.; Segard, J.; Erb, A. M.; Aponick, A. Catalytic Dehydrative Lactonization of Allylic Alcohols. Organic letters 2018, 20, 3034–3038. doi:10.1021/acs.orglett.8b01063
• Tikad, A.; Delbrouck, J. A.; Vincent, S. P. Debenzylative Cycloetherification: An Overlooked Key Strategy for Complex Tetrahydrofuran Synthesis. Chemistry (Weinheim an der Bergstrasse, Germany) 2016, 22, 9456–9476. doi:10.1002/chem.201600655
• Manoni, E.; Daka, M.; Mastandrea, M. M.; De Nisi, A.; Monari, M.; Bandini, M. Catalytic α‐Allylation of Enones with Alcohols via [Gold(I)]‐Mediated [3,3]‐Sigmatropic Rearrangement of Propargylic Carboxylates. Advanced Synthesis & Catalysis 2016, 358, 1404–1409. doi:10.1002/adsc.201600113
• Quintavalla, A.; Bandini, M. Gold‐Catalyzed Allylation Reactions. ChemCatChem 2016, 8, 1437–1453. doi:10.1002/cctc.201600071
• Barker, G.; Johnson, D. G.; Young, P. C.; MacGregor, S.; Lee, A.-L. Chirality Transfer in Gold(I)-Catalysed Direct Allylic Etherifications of Unactivated Alcohols: Experimental and Computational Study. Chemistry (Weinheim an der Bergstrasse, Germany) 2015, 21, 13748–13757. doi:10.1002/chem.201501607
• Webster, S.; Young, P. C.; Barker, G.; Rosair, G. M.; Lee, A.-L. Dehydrative Thiolation of Allenols: Indium vs Gold Catalysis. The Journal of organic chemistry 2015, 80, 1703–1708. doi:10.1021/jo502648w
• Herkert, L.; Green, S. L. J.; Barker, G.; Johnson, D. G.; Young, P. C.; MacGregor, S.; Lee, A.-L. Gold(I)‐Catalysed Direct Thioetherifications Using Allylic Alcohols: an Experimental and Computational Study. Chemistry (Weinheim an der Bergstrasse, Germany) 2014, 20, 11540–11548. doi:10.1002/chem.201403293
• Wright, J. R.; Young, P. C.; Lucas, N. T.; Lee, A.-L.; Crowley, J. D. Gold(I) and Palladium(II) Complexes of 1,3,4-Trisubstituted 1,2,3-Triazol-5-ylidene “Click” Carbenes: Systematic Study of the Electronic and Steric Influence on Catalytic Activity. Organometallics 2013, 32, 7065–7076. doi:10.1021/om400773n
• Yoshida, M.; Nozaki, T.; Nemoto, T.; Hamada, Y. Formal meta-specific intramolecular Friedel–Crafts allylic alkylation of phenols through a spirocyclization–dienone–phenol rearrangement cascade. Tetrahedron 2013, 69, 9609–9615. doi:10.1016/j.tet.2013.09.042
• Ketcham, J. M.; Cardoso, F. S. P.; Biannic, B.; Piras, H.; Aponick, A. Nitrogen Nucleophiles in Au‐Catalyzed Dehydrative Cyclization Reactions. Israel Journal of Chemistry 2013, 53, 923–931. doi:10.1002/ijch.201300041
• Mukherjee, P.; Widenhoefer, R. A. The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex. Chemistry (Weinheim an der Bergstrasse, Germany) 2013, 19, 3437–3444. doi:10.1002/chem.201203987
• Bandini, M.; Bottoni, A.; Chiarucci, M.; Cera, G.; Miscione, G. P. Mechanistic Insights into Enantioselective Gold-Catalyzed Allylation of Indoles with Alcohols: The Counterion Effect. Journal of the American Chemical Society 2012, 134, 20690–20700. doi:10.1021/ja3086774

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