Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Gold(I)-catalyzed Cycloisomerization of the Mixed N,S-acetals Generated from Homopropargylic Amines; Mechanistic Implication for the Formal Alkyne Prins Reaction

  • Kim, Cheol-Jae (Department of Chemistry, POSTECH (Pohang University of Science and Technology)) ;
  • Lim, Won-Taeck (Department of Chemistry, POSTECH (Pohang University of Science and Technology)) ;
  • Rhee, Young-Ho (Department of Chemistry, POSTECH (Pohang University of Science and Technology))
  • Received : 2010.04.01
  • Accepted : 2010.04.08
  • Published : 2010.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Michael, J. P. Nat. Prod. Rep. 2008, 25, 139. https://doi.org/10.1039/b612166g
  2. Hashmi, A. S. K.; Rudolph, M. Chem. Soc. Rev. 2008, 37, 1766. https://doi.org/10.1039/b615629k
  3. Arcadi, A. Chem. Rev. 2008, 108, 3266. https://doi.org/10.1021/cr068435d
  4. Li, Z.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239. https://doi.org/10.1021/cr068434l
  5. Gorin, D. J.; Sherry,B. D.; Toste, F. D. Chem. Rev. 2008, 108, 3351. https://doi.org/10.1021/cr068430g
  6. Kim, C.; Bae, H. J.; Lee, J. H.; Jeong, W.; Kim, H.; Sampath, V.;Rhee, Y. H. J. Am. Chem. Soc. 2009, 131, 14660. https://doi.org/10.1021/ja906744r
  7. Nakamura, I.; Sato, T.; Terada, M.; Yamamoto, Y. Org. Lett. 2008, 10, 2649. https://doi.org/10.1021/ol8007556
  8. Dube, P.; Toste, F. D. J. Am. Chem. Soc. 2006,128, 12062. https://doi.org/10.1021/ja064209+
  9. Bae, H. J.; Baskar, B.; An, S. E.; Cheong, J. Y.;Thangadurai, D. T.; Hwang, I.-C.; Rhee, Y. H. Angew. Chem., Int. Ed. 2008, 47, 2263. https://doi.org/10.1002/anie.200705117
  10. Clive, D. L.; Li, Z.; Yu, M. J. Org. Chem. 2007, 72, 5608 https://doi.org/10.1021/jo070664s
  11. Yadav, A. K.; Peruncheralathan, S.; Ila, H.; Junjappa, H. J. Org. Chem. 2007, 72, 1388. https://doi.org/10.1021/jo062302a
  12. Ohno, H.; Mizutani, T.; Kadoh, Y.; Aso, A.; Miyaura, K.; Fuji, N.;Tanaka, T. J. Org. Chem. 2007, 72, 4378. https://doi.org/10.1021/jo0700528
  13. Miranda, P. O.; Carballo, R. M.; Martín, V. S.; Padron, J. I. Org. Lett. 2009, 11, 357. https://doi.org/10.1021/ol802593u
  14. Franzman, M. A.; Barrios, A. M. Inorg. Chem. 2008, 47, 3928. https://doi.org/10.1021/ic800157t

Cited by

  1. ChemInform Abstract: Gold(I)‐Catalyzed Cycloisomerization of the Mixed N,S‐Acetals Generated from Homopropargylic Amines; Mechanistic Implication for the Formal Alkyne Prins Reaction. vol.41, pp.46, 2010, https://doi.org/10.1002/chin.201046139
  2. Gold(I)‐Catalyzed Access to Tetrahydropyran‐4‐ones from 4‐(Alkoxyalkyl)oxy‐1‐butynes: Formal Catalytic Petasis–Ferrier Rearrangement vol.17, pp.5, 2010, https://doi.org/10.1002/chem.201002918
  3. A Ru-catalyzed one-pot synthesis of homopropargylic amines from alkyl azides under photolytic conditions vol.4, pp.40, 2010, https://doi.org/10.1039/c4ra02941k
  4. 1,2- N -Migration in a Gold-Catalysed Synthesis of Functionalised Indenes by the 1,1-Carboalkoxylation of Ynamides vol.20, pp.24, 2014, https://doi.org/10.1002/chem.201403040
  5. Polyoxometalate-Gold(I)/H+ Complexes: Air-Stable, Efficient, Polyvalent, and Bifunctional Catalysts vol.34, pp.20, 2010, https://doi.org/10.1021/acs.organomet.5b00656
  6. Gold-Catalyzed Asymmetric Thioallylation of Propiolates via Charge-Induced Thio-Claisen Rearrangement vol.142, pp.49, 2020, https://doi.org/10.1021/jacs.0c09783