Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Organocatalytic Enantioselective α-Alkylation of Cyclic Ketones by SN1-Type Reaction of Alcohols

  • Received : 2011.01.02
  • Accepted : 2011.01.28
  • Published : 2011.04.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol 2, Cahpter 1.1
  2. Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol 3, pp 1-110.
  3. Job, A.; Janeck, C. F.; Bettray, W.; Peters, R.; Enders, D. Tetrahedron 2002, 58, 2253. https://doi.org/10.1016/S0040-4020(02)00080-7
  4. Vignola, N.; List, B. J. Am. Chem. Soc. 2004, 126, 450. https://doi.org/10.1021/ja0392566
  5. Fu, A.; List, B.; Thiel, W. J. Org. Chem. 2006, 71, 320. https://doi.org/10.1021/jo052088a
  6. Shaikh, R. R.; Mazzanti, A.; Petrini, M.; Bartoli, G.; Melchiorre, P. Angew. Chem. Int. Ed. 2008, 47, 8707. https://doi.org/10.1002/anie.200803947
  7. Cozzi, P. G.; Zoli, L. Angew. Chem. Int. Ed. 2008, 47, 4162. https://doi.org/10.1002/anie.200800622
  8. Cozzi, P. G.; Benfatti, F.; Zoli, L. Angew. Chem. Int. Ed. 2009, 48, 1313. https://doi.org/10.1002/anie.200805423
  9. Zhang, L.; Cui, L.; Li, X.; Li, J.; Luo, S.; Cheng, J.-P. Eur. J. Org. Chem. 2010, 4876.
  10. Zhang, L.; Cui, L.; Li, X.; Li, J.; Luo, S.; Cheng, J.-P. Chem. Eur. J. 2010, 16, 2045. https://doi.org/10.1002/chem.200902509
  11. Kim, D. Y.; Huh, S. C.; Kim, S. M. Tetrahedron Lett. 2001, 42, 6299. https://doi.org/10.1016/S0040-4039(01)01237-0
  12. Kim, D. Y.; Huh, S. C. Tetrahedron 2001, 57, 8933. https://doi.org/10.1016/S0040-4020(01)00891-2
  13. Kim, D. Y.; Park, E. J. Org. Lett. 2002, 4, 545. https://doi.org/10.1021/ol010281v
  14. Kim, S. M.; Kim, H. R.; Kim, D. Y. Org. Lett. 2005, 7, 2309. https://doi.org/10.1021/ol050413a
  15. Kang, Y. K.; Kim, D. Y. Tetrahedron Lett. 2006, 47, 4565. https://doi.org/10.1016/j.tetlet.2006.05.003
  16. Mang, J. Y.; Kwon, D. G.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 259. https://doi.org/10.1016/j.jfluchem.2008.11.001
  17. Kang, Y. K; Cho, M. J.; Kim, S. M.; Kim, D. Y. Synlett 2007, 1135.
  18. Lee, J. H.; Bang, H. T.; Kim, D. Y. Synlett 2008, 1821.
  19. Kim, S. M.; Lee, J. H.; Kim, D. Y. Synlett 2008, 2659.
  20. Jung, S. H.; Kim, D. Y. Tetrahedron Lett. 2008, 49, 5527. https://doi.org/10.1016/j.tetlet.2008.07.041
  21. Kang, S. H.; Kang, Y. K.; Kim, D. Y. Tetrahedron 2009, 65, 5676. https://doi.org/10.1016/j.tet.2009.05.037
  22. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734. https://doi.org/10.1021/jo900880t
  23. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779. https://doi.org/10.1002/adsc.200900268
  24. Kwon, B. K.; Kim, S. M.; Kim, D. Y. J. Fluorine Chem. 2009, 130, 759. https://doi.org/10.1016/j.jfluchem.2009.06.002
  25. Oh, Y.; Kim, S. M.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4674. https://doi.org/10.1016/j.tetlet.2009.06.003
  26. Moon, H. W.; Cho, M. J.; Kim, D. Y. Tetrahedron Lett. 2009, 50, 4896. https://doi.org/10.1016/j.tetlet.2009.06.056
  27. Kang, Y. K.; Kim, D. Y. J. Org. Chem. 2009, 74, 5734. https://doi.org/10.1021/jo900880t
  28. Lee, J. H.; Kim, D. Y. Adv. Synth. Catal. 2009, 351, 1779. https://doi.org/10.1002/adsc.200900268
  29. Kim, E. J.; Kang, Y. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1437. https://doi.org/10.5012/bkcs.2009.30.7.1437
  30. Kang, S. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1439. https://doi.org/10.5012/bkcs.2009.30.7.1439
  31. Kwon, B. K.; Kim, D. Y. Bull. Korean Chem. Soc. 2009, 30, 1441. https://doi.org/10.5012/bkcs.2009.30.7.1441
  32. Kang, Y. K.; Kim, D. Y. Curr. Org. Chem. 2010, 14, 917. https://doi.org/10.2174/138527210791111768
  33. Kang, S. H.; Kim, D. Y. Adv. Synth. Catal. 2010, 352, 2783. https://doi.org/10.1002/adsc.201000515
  34. Kang, Y. K.; Kim, S. M.; Kim, D. Y. J. Am. Chem. Soc. 2010, 132, 11847. https://doi.org/10.1021/ja103786c
  35. Lee, J. H.; Kim, D. Y. Synthesis 2010, 1860.
  36. Moon, H. W.; Kim, D. Y. Tetrahedron Lett. 2010, 51, 2906. https://doi.org/10.1016/j.tetlet.2010.03.105
  37. Park, E. J.; Kim, M. H.; Kim, D. Y. J. Org. Chem. 2004, 69, 6897. https://doi.org/10.1021/jo0401772
  38. Mayr, H.; Kempf, B.; Ofial, A. R. Acc. Chem. Res. 2003, 36, 66. https://doi.org/10.1021/ar020094c

Cited by

  1. 1-Type Reaction of Alcohols. vol.42, pp.38, 2011, https://doi.org/10.1002/chin.201138026
  2. -Benzylic Sulfonamides through Carbon–Nitrogen Bond Cleavage vol.76, pp.19, 2011, https://doi.org/10.1021/jo2014142
  3. Enantioselective Conjugate Addition of 4-Hydroxycoumarin to Enones Catalyzed by Binaphthyl-Modified Primary Amine Organocatalyst vol.33, pp.6, 2012, https://doi.org/10.5012/bkcs.2012.33.6.1825
  4. Enantioselective Michael Addition of 2-Hydroxy-1,4-naphthoquinone to β,γ-Unsaturated α-Keto Esters Catalyzed by Binaphthyl-Modified Squaramide vol.34, pp.6, 2013, https://doi.org/10.5012/bkcs.2013.34.6.1619
  5. Enantioselective Direct α-Amination of Aromatic Ketones Catalyzed by Binaphthyl-Modified Primary Amine vol.34, pp.7, 2013, https://doi.org/10.5012/bkcs.2013.34.7.1955
  6. Organocatalytic Enantioselective Michael Addition of Silyl Malonate to α,β-Unsaturated Enones: One-pot Synthesis of Chiral δ-Keto Esters vol.34, pp.9, 2013, https://doi.org/10.5012/bkcs.2013.34.9.2569
  7. Identification of Polo-Like Kinase 1 Inhibitors Using Structure-Based Molecular Design vol.35, pp.7, 2014, https://doi.org/10.5012/bkcs.2014.35.7.1929
  8. Triflic Acid Promoted Direct α-Alkylation of Unactivated Ketones Using Benzylic Alcohols via in Situ Formed Acetals vol.79, pp.13, 2014, https://doi.org/10.1021/jo500759a
  9. Thiourea-catalyzed Intramolecular Allylic Amination: Synthesis of Dihydroquinoline Derivatives vol.36, pp.1, 2015, https://doi.org/10.1002/bkcs.10014
  10. Organocatalytic Asymmetric Michael Addition of α-Fluoro β-Ketophosphonate to Nitroalkenes vol.36, pp.12, 2015, https://doi.org/10.1002/bkcs.10580
  11. Diastereo- and Enantioselective Conjugate Addition of 3-Chlorooxindoles to Nitroalkenes Catalyzed by Binaphthyl-modified Organocatalyst vol.36, pp.5, 2015, https://doi.org/10.1002/bkcs.10264
  12. Diastereo- and Enantioselective Conjugate Addition of α-Substituted Cyanoacetates to Maleimides Catalyzed by Binaphthyl-based Thiourea vol.36, pp.9, 2015, https://doi.org/10.1002/bkcs.10439
  13. Catalytic Enantioselective Alkylation of β-Keto Esters with Xanthydrol in the Presence of Chiral Palladium Complex vol.37, pp.1, 2016, https://doi.org/10.1002/bkcs.10628
  14. Construction of an all-carbon quaternary stereocenter by organocatalytic enantioselective α-functionalization of α-substituted β-ketocarbonyls with electron deficient vinylarenes vol.51, pp.56, 2015, https://doi.org/10.1039/C5CC03562G
  15. -Symmetric diamines and their derivatives as promising organocatalysts for asymmetric synthesis vol.84, pp.11, 2015, https://doi.org/10.1070/RCR4562
  16. Enantioselective Michael Addition of 3-Aryl-Substituted Oxindoles to Methyl Vinyl Ketone Catalyzed by a Binaphthyl-Modified Bifunctional Organocatalyst vol.17, pp.6, 2012, https://doi.org/10.3390/molecules17067523
  17. Catalytic Enantioselective Fluorination of α-Cyanosulfones in the Presence of Chiral Palladium Complexes vol.33, pp.8, 2012, https://doi.org/10.5012/bkcs.2012.33.8.2481
  18. Organocatalytic Asymmetric Conjugate Addition of 3-Alkyl-Substituted Oxindoles to Vinyl Ketones vol.33, pp.10, 2011, https://doi.org/10.5012/bkcs.2012.33.10.3171
  19. Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to β,γ-Unsaturated α-Keto Esters vol.33, pp.11, 2011, https://doi.org/10.5012/bkcs.2012.33.11.3537
  20. Organocatalytic enantioselective decarboxylative Michael addition of β-ketoacids to α,β-unsaturated ketones vol.3, pp.5, 2011, https://doi.org/10.1039/c2ra21945j
  21. Organocatalytic Asymmetric Michael Addition of 1,3-Cyclohexanedione to Benzylidenemalonitriles vol.35, pp.1, 2011, https://doi.org/10.5012/bkcs.2014.35.1.98
  22. Discovery of FAK Inhibitors Using Structure Based Drug Design vol.35, pp.11, 2011, https://doi.org/10.5012/bkcs.2014.35.11.3156