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Gold-catalyzed post-Ugi ipso-cyclization with switchable diastereoselectivity

(2018) JOURNAL OF ORGANIC CHEMISTRY. 83(15). p.8170-8182
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Abstract
A gold-catalyzed post-Ugi ipso-cyclization for the diastereoselective synthesis of spirocyclic pyrrol-2-one-dienone system is described. Tuning the catalytic system, solvent, and temperature allowed selectively attaining two sets of diastereoisomers. The scope of the process has been evaluated, and a putative mechanistic model was proposed.
Keywords
MICHAEL CASCADE REACTION, N-ARYL ALKYNAMIDES, ONE-POT SYNTHESIS, INTRAMOLECULAR HYDROARYLATION, SELECTIVE SYNTHESIS, PASSERINI REACTIONS, DOMINO CYCLIZATION, BETA-LACTAMS, ALKYNES, DEAROMATIZATION

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Citation

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MLA
Nechaev, Anton A et al. “Gold-catalyzed post-Ugi Ipso-cyclization with Switchable Diastereoselectivity.” JOURNAL OF ORGANIC CHEMISTRY 83.15 (2018): 8170–8182. Print.
APA
Nechaev, A. A., Van Hecke, K., Zaman, M., Kashtanov, S., Ungur, L., Pereshivko, O. P., Peshkov, V. A., et al. (2018). Gold-catalyzed post-Ugi ipso-cyclization with switchable diastereoselectivity. JOURNAL OF ORGANIC CHEMISTRY, 83(15), 8170–8182.
Chicago author-date
Nechaev, Anton A, Kristof Van Hecke, Manzoor Zaman, Stepan Kashtanov, Liviu Ungur, Olga P Pereshivko, Vsevolod A Peshkov, and Erik V Van der Eycken. 2018. “Gold-catalyzed post-Ugi Ipso-cyclization with Switchable Diastereoselectivity.” Journal of Organic Chemistry 83 (15): 8170–8182.
Chicago author-date (all authors)
Nechaev, Anton A, Kristof Van Hecke, Manzoor Zaman, Stepan Kashtanov, Liviu Ungur, Olga P Pereshivko, Vsevolod A Peshkov, and Erik V Van der Eycken. 2018. “Gold-catalyzed post-Ugi Ipso-cyclization with Switchable Diastereoselectivity.” Journal of Organic Chemistry 83 (15): 8170–8182.
Vancouver
1.
Nechaev AA, Van Hecke K, Zaman M, Kashtanov S, Ungur L, Pereshivko OP, et al. Gold-catalyzed post-Ugi ipso-cyclization with switchable diastereoselectivity. JOURNAL OF ORGANIC CHEMISTRY. 2018;83(15):8170–82.
IEEE
[1]
A. A. Nechaev et al., “Gold-catalyzed post-Ugi ipso-cyclization with switchable diastereoselectivity,” JOURNAL OF ORGANIC CHEMISTRY, vol. 83, no. 15, pp. 8170–8182, 2018.
@article{8581222,
  abstract     = {A gold-catalyzed post-Ugi ipso-cyclization for the diastereoselective synthesis of spirocyclic pyrrol-2-one-dienone system is described. Tuning the catalytic system, solvent, and temperature allowed selectively attaining two sets of diastereoisomers. The scope of the process has been evaluated, and a putative mechanistic model was proposed.},
  author       = {Nechaev, Anton A and Van Hecke, Kristof and Zaman, Manzoor and Kashtanov, Stepan and Ungur, Liviu and Pereshivko, Olga P and Peshkov, Vsevolod A and Van der Eycken, Erik V},
  issn         = {0022-3263},
  journal      = {JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {MICHAEL CASCADE REACTION,N-ARYL ALKYNAMIDES,ONE-POT SYNTHESIS,INTRAMOLECULAR HYDROARYLATION,SELECTIVE SYNTHESIS,PASSERINI REACTIONS,DOMINO CYCLIZATION,BETA-LACTAMS,ALKYNES,DEAROMATIZATION},
  language     = {eng},
  number       = {15},
  pages        = {8170--8182},
  title        = {Gold-catalyzed post-Ugi ipso-cyclization with switchable diastereoselectivity},
  url          = {http://dx.doi.org/10.1021/acs.joc.8b00953},
  volume       = {83},
  year         = {2018},
}

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