Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones

Chunhui Jiang, Fangrui Zhong and Yixin Lu
Beilstein J. Org. Chem. 2012, 8, 1279–1283. https://doi.org/10.3762/bjoc.8.144

Supporting Information

Supporting Information File 1: Characterization data and spectra of synthesized compounds.
Format: PDF Size: 2.8 MB Download

Cite the Following Article

Asymmetric organocatalytic decarboxylative Mannich reaction using β-keto acids: A new protocol for the synthesis of chiral β-amino ketones
Chunhui Jiang, Fangrui Zhong and Yixin Lu
Beilstein J. Org. Chem. 2012, 8, 1279–1283. https://doi.org/10.3762/bjoc.8.144

How to Cite

Jiang, C.; Zhong, F.; Lu, Y. Beilstein J. Org. Chem. 2012, 8, 1279–1283. doi:10.3762/bjoc.8.144

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

  • Majumdar, N. Carboxylic Acids as Building Blocks in Catalytic Asymmetric Reactions. ACS Catalysis 2022, 12, 8291–8324. doi:10.1021/acscatal.2c02410
  • Xavier, T.; Condon, S.; Pichon, C.; Le Gall, E.; Presset, M. Substituted Malonic Acid Half Oxyesters (SMAHOs): Green Nucleophiles for Organic Synthesis. European Journal of Organic Chemistry 2022, 2022. doi:10.1002/ejoc.202101392
  • Tang, Y.; Liu, K.; Wu, Y.; Zhou, S.; Cheng, T.; Liu, G. Single‐Operation Decarboxylative Mannich Reaction/Asymmetric Transfer Hydrogenation Cascade Process Directly Accesses 1,3‐Distereocentered β‐Sulfonamido Alcohols. Advanced Synthesis & Catalysis 2022, 364, 994–1001. doi:10.1002/adsc.202101418
  • Qin, W.; Subhani, M.; Jiang, C.; Lu, H. β-Keto acids in asymmetric metal catalysis and organocatalysis. Organic & biomolecular chemistry 2021, 19, 10030–10046. doi:10.1039/d1ob01481a
  • Zhang, C.-C.; Chen, L.-J.; Shen, B.-C.; Xie, H.-D.; Li, W.; Sun, Z.-W. Enantioselective decarboxylative Mannich reaction of β-keto acids with C-alkynyl N-Boc N,O-acetals: access to chiral β-keto propargylamines. Organic & biomolecular chemistry 2021, 19, 8607–8612. doi:10.1039/d1ob01555a
  • Guan, R.; Hsu, C.; Han, J. Trifluoroethanol‐mediated Decarboxylative Addition Reactions of β‐Ketoacids with Diverse Electrophiles. Asian Journal of Organic Chemistry 2020, 10, 273–284. doi:10.1002/ajoc.202000553
  • Paul, A.; Kim, J. H.; Daniel, S. D.; Seidel, D. Diversification of Unprotected Alicyclic Amines by C−H Bond Functionalization: Decarboxylative Alkylation of Transient Imines. Angewandte Chemie (International ed. in English) 2020, 60, 1625–1628. doi:10.1002/anie.202011641
  • Paul, A.; Kim, J. H.; Daniel, S. D.; Seidel, D. Diversification of Unprotected Alicyclic Amines by C−H Bond Functionalization: Decarboxylative Alkylation of Transient Imines. Angewandte Chemie 2020, 133, 1649–1652. doi:10.1002/ange.202011641
  • Hu, H.; Wang, C.; Lai, H.; Wang, S.; Ni, H.-L.; Yu, W.; Cao, P. The Fe(III)-catalyzed decarboxylative cycloaddition of β-ketoacids and 2H-azirines for the synthesis of pyrrole derivatives. Organic Chemistry Frontiers 2020, 7, 3686–3691. doi:10.1039/d0qo00951b
  • Niu, J.-P.; Nie, J.; Li, S.; Ma, J.-A. Organocatalytic asymmetric synthesis of β,β-diaryl ketones via one-pot tandem dehydration/1,6-addition/decarboxylation transformation of β-keto acids and 4-hydroxybenzyl alcohols. Chemical communications (Cambridge, England) 2020, 56, 8687–8690. doi:10.1039/d0cc02213f
  • Jiang, C.; Chen, Y.; Zhang, H.; Tan, J.-P.; Wang, T. L. Catalyst-Free Synthesis of α-Functionalized 2H-Chromenes in Water: A Tandem Self-Promoted pseudo-Substitution and Decarboxylation Process. Chemistry, an Asian journal 2019, 14, 2938–2944. doi:10.1002/asia.201900641
  • Zhou, Y.; You, Y.; Wang, Z.-H.; Zhang, X.-M.; Xu, X.-Y.; Yuan, W.-C. Organocatalyzed Enantioselective Decarboxylative Mannich Reaction of β‐Ketoacids with Pyrazolinone Ketimines for the Construction of Chiral β‐Amino Ketone‐Pyrazolinone Derivatives. European Journal of Organic Chemistry 2019, 2019, 3112–3116. doi:10.1002/ejoc.201900346
  • Liu, Y.-J.; Li, J.-S.; Nie, J.; Ma, J.-A. Organocatalytic Asymmetric Decarboxylative Mannich Reaction of β-Keto Acids with Cyclic α-Ketiminophosphonates: Access to Quaternary α-Aminophosphonates. Organic letters 2018, 20, 3643–3646. doi:10.1021/acs.orglett.8b01422
  • Schwarz, J.; König, B. Decarboxylative reactions with and without light – a comparison. Green Chemistry 2018, 20, 323–361. doi:10.1039/c7gc02949g
  • Vamisetti, G. B.; Chowdhury, R.; Ghosh, S. K. Organocatalytic decarboxylative aldol reaction of β-ketoacids with α-ketophosphonates en route to the enantioselective synthesis of tertiary α-hydroxyphosphonates. Organic & biomolecular chemistry 2017, 15, 3869–3873. doi:10.1039/c7ob00796e
  • Wei, Y.; Zhang, H.-X.; Zeng, J.-L.; Nie, J.; Ma, J.-A. Organocatalytic Asymmetric Decarboxylative Amination of β-Keto Acids: Access to Optically Active α-Amino Ketones and 1,2-Amino Alcohols. Organic letters 2017, 19, 2162–2165. doi:10.1021/acs.orglett.7b00797
  • Sun, Y.-L.; Wei, Y.; Shi, M. Applications of Chiral Thiourea-Amine/Phosphine Organocatalysts in Catalytic Asymmetric Reactions. ChemCatChem 2017, 9, 718–727. doi:10.1002/cctc.201601144
  • Liu, P.; Zhang, G.; Sun, P. Transition metal-free decarboxylative alkylation reactions. Organic & biomolecular chemistry 2016, 14, 10763–10777. doi:10.1039/c6ob02101h
  • Cui, X.-Y.; Duan, H.-X.; Zhang, Y.; Wang, Y.-Q. Asymmetric Mannich Reaction of Aryl Methyl Ketones with Cyclic Imines Benzo[e][1,2,3]oxathiazine 2,2-Dioxides Catalyzed by Cinchona Alkaloid-based Primary Amines. Chemistry, an Asian journal 2016, 11, 3118–3125. doi:10.1002/asia.201601149
  • Wei, Y.; Guo, R.; Dang, Y.; Nie, J.; Ma, J.-A. Organocatalytic Enantioselective Decarboxylative Michael Addition of β-Keto Acids to Dicyanoolefins and Disulfonylolefins. Advanced Synthesis & Catalysis 2016, 358, 2721–2726. doi:10.1002/adsc.201600485
Other Beilstein-Institut Open Science Activities