DOI QR코드

DOI QR Code

Synthesis of Chromane Derivatives by Palladium-Catalyzed Intramolecular Allylation of Aldehydes with Allylic Acetates or Chlorides Using Indium and Indium(III) Chloride

  • Nguyen, Van Cuong (Department of Chemistry and Institute of Basic Sciences, Chungbuk National University) ;
  • Kim, Yong-Tae (Department of Chemistry and Institute of Basic Sciences, Chungbuk National University) ;
  • Yu, Yeon-Kwon (Department of Chemistry and Institute of Basic Sciences, Chungbuk National University) ;
  • Kang, Han-Young (Department of Chemistry and Institute of Basic Sciences, Chungbuk National University)
  • Published : 2005.05.20

Abstract

Keywords

References

  1. Tocopherol A: Solladie, G.; Moine, G. J. Am. Chem. Soc. 1984, 106, 6097 https://doi.org/10.1021/ja00332a066
  2. Calanolide A: Chenera, B.; West, M. L.; Finkelstein, J. A.; Dreyer, G. B. J. Org. Chem. 1993, 58, 5605 https://doi.org/10.1021/jo00073a015
  3. Rao, A. V. R.; Gaitonde, A. S.; Prakash, K. R. C.; Rao, S. P. Tetrahedron Letters 1994, 35, 6347 https://doi.org/10.1016/S0040-4039(00)73429-0
  4. Partial estrogens: Bury, P. S.; Christiansen, L. B.; Jacobsen, P.; Jorgensen, A. S.; Kanstrup, A.; Naerum, L.; Bain, S.; Fledelius, C.; Gissel, B.; Hansen, B. S.; Korsgaard, N.; Thorpe, S. M.; Wasserman, K. Bioorg. Med. Chem. 2002, 10, 125 https://doi.org/10.1016/S0968-0896(01)00257-7
  5. Kang, H.-Y.; Kim, Y.-T.; Yu, Y.-K.; Cha, J. H.; Cho, Y. S.; Koh, H. Y. Synlett 2004, 45
  6. Cha, J. H.; Cho, Y. S.; Koh, H. Y.; Lee, E.; Kim, Y.-T.; Yang, H.- H.; Kang, H.-Y. Bull. Korean Chem. Soc. 2004, 25, 1123 https://doi.org/10.5012/bkcs.2004.25.8.1123
  7. Kang, H.-Y.; Yu, Y.-K. Bull. Korean Chem. Soc. 2004, 25, 1627 https://doi.org/10.5012/bkcs.2004.25.11.1627
  8. Araki, S.; Kamei, T.; Hirachita, T.; Yamamura, H.; Kawai, M. Org. Lett. 2000, 2, 847 https://doi.org/10.1021/ol005610i
  9. Jang, T.-S.; Keum, G.; Kang, S.-B.; Chung, B.-Y.; Kim, Y. Synthesis 2003, 5, 775
  10. Hirashita, T.; Kambe, S.; Tsuki, H.; Omori, H.; Araki, S. J. Org. Chem. 2004, 69, 5054 https://doi.org/10.1021/jo049394t
  11. Lee, P. H.; Seomoon, D.; Lee, K.; Kim, S.; Kim, H.; Kim, H.; Shim, E.; Lee, M.; Lee, S.; Kim, M.; Sridbar, M. Adv. Synth. Catal. 2004, 346, 1641 https://doi.org/10.1002/adsc.200404125
  12. Shin, J. A.; Choi, K. I.; Pae, A. N.; Koh, H. Y.; Kang, H.-Y.; Cho, Y. S. J. Chem. Soc. Perkin Trans. 1 2001, 946
  13. Shin, J. A.; Cha, J. W.; Pae, A. N.; Choi, K. I.; Koh, H. Y.; Kang, H.-Y.; Cho, Y. S. Tetrahedron Lett. 2001, 42, 5489 https://doi.org/10.1016/S0040-4039(01)01064-4

Cited by

  1. Organoindium Reagents: The Preparation and Application in Organic Synthesis vol.113, pp.1, 2013, https://doi.org/10.1021/cr300051y
  2. Cooperative Titanocene and Phosphine Catalysis: Accelerated C–X Activation for the Generation of Reactive Organometallics vol.78, pp.2, 2013, https://doi.org/10.1021/jo301726v
  3. Asymmetric palladium-catalyzed umpolung cyclization of allylic acetate-aldehyde using formate as a reductant vol.51, pp.38, 2015, https://doi.org/10.1039/C5CC02176F
  4. Inter- and Intramolecular Palladium-Catalyzed Allyl Cross-Coupling Reactions Using Allylindium Generated In Situ from Allyl Acetates, Indium, and Indium Trichloride vol.13, pp.18, 2007, https://doi.org/10.1002/chem.200601338
  5. Synthesis of Chromane Derivatives by Palladium-Catalyzed Intramolecular Allylation of Aldehydes with Allylic Acetates or Chlorides Using Indium and Indium(III) Chloride. vol.36, pp.40, 2005, https://doi.org/10.1002/chin.200540151
  6. Indium-mediated Allylation of α-Imino Esters in Aqueous Media vol.28, pp.1, 2007, https://doi.org/10.5012/bkcs.2007.28.1.139
  7. Intramolecular Umpolung Allylation of Imines vol.20, pp.18, 2005, https://doi.org/10.1021/acs.orglett.8b02536
  8. Palladium‐Catalyzed Umpolung Type‐II Cyclization of Allylic Carbonate‐Aldehydes Leading to 3‐Methylenecycloalkanol Derivatives vol.361, pp.16, 2005, https://doi.org/10.1002/adsc.201900450
  9. Key Factors for High Diastereo- and Enantioselectivity of Umpolung Cyclizations of Aldehyde-Containing Allylpalladium Intermediates vol.92, pp.10, 2005, https://doi.org/10.1246/bcsj.20190167
  10. InCl3: A Versatile Catalyst for Synthesizing a Broad Spectrum of Heterocycles vol.5, pp.6, 2005, https://doi.org/10.1021/acsomega.9b03686
  11. Computational insight into the mechanism and origin of high regioselectivity in the ring-opening cyclization of spirocyclopropanes with stabilized sulfonium ylides by the DFT vol.26, pp.9, 2005, https://doi.org/10.1007/s00894-020-04522-1