Catalytic in situ generation of Zn(II)-alkynilides under mild conditions: A novel C=N addition process utilizing terminal acetylenes [12]

Journal of the American Chemical Society

Volumn 121, Issue 48, 1999, Pages 11245-11246

  Frantz, Doug E ^a   Fässler, Roger ^a   Carreira, Erick M ^a  

^a ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE DERIVATIVE; PROPARGYL HYDROXYLAMINE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

CATALYSIS; CHEMICAL BOND; COMPLEX FORMATION; LETTER; STOICHIOMETRY; SYNTHESIS; THERMODYNAMICS;

EID: 0033537047     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993074n     Document Type: Letter

References (36)

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9. For key references to addition reactions employing stannyl, silylated, and boryl reagents: (a) Yamamoto, Y,; Nishii, S.; Maruyama, K. J. Chem. Soc., Chem. Commun. 1986, 102. (b) Corey, E. J.; Cimprich, K. A. J. Am. Chem. Soc. 1994, 116, 3151. (c) Ahn, J. H.; Joung. M. J.; Yoon, N. M. J. Org. Chem. 1995, 60, 6173. (d) Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1999. 40, 4461. For general references, see: (e) Santelli, M.; Pons, J.-M. Lewis Acids and Selectivity in Organic Synthesis; CRC: Boca Raton, FL, 1996; Chapters 3 and 5. (f) Marshall, J. A. Chem. Rev. 1996, 96, 31. (g) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 22, 07.
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13. (b) During the preparation of this manuscript, an important, novel process was reported for the addition of terminal acetylenes to aliphatic aldehydes and ketones utilizing 10 mol % CsOH in DMSO, see: Tzalis, D.; Knochel, P. Angew. Chem., Int. Ed. 1999, 38, 1463.
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27. For a recent report of the addition of silyl ketene acelals to nitrones, see: (a) Ohtake, H.; Imada, Y.; Murahashi, S. I. J. Org. Chem. 1999, 64, 3790. For highly diastereoselective additions to chiral ketimines, see: (b) Cogan, D. A.; Ellman, J. J. Am. Chem. Soc. 1999, 121, 268. (c) Liu, G.; Cogan, D.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913. (d) Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011. (e) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
28. For a recent report of the addition of silyl ketene acelals to nitrones, see: (a) Ohtake, H.; Imada, Y.; Murahashi, S. I. J. Org. Chem. 1999, 64, 3790. For highly diastereoselective additions to chiral ketimines, see: (b) Cogan, D. A.; Ellman, J. J. Am. Chem. Soc. 1999, 121, 268. (c) Liu, G.; Cogan, D.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913. (d) Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011. (e) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
29. For a recent report of the addition of silyl ketene acelals to nitrones, see: (a) Ohtake, H.; Imada, Y.; Murahashi, S. I. J. Org. Chem. 1999, 64, 3790. For highly diastereoselective additions to chiral ketimines, see: (b) Cogan, D. A.; Ellman, J. J. Am. Chem. Soc. 1999, 121, 268. (c) Liu, G.; Cogan, D.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913. (d) Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011. (e) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13.
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31. 2O in DMF at 80°C the addition of acetylenes to nitrones has been reported to give alkynyl imines in a reaction that may proceed through the initial formation of a dipolar cycloadduct. The acetylenes and nitrone substrates examined in the study were primarily derived from aromatic aldehydes and aryl alkynes, see: Miura, M.; Enna, M.; Okuro, K.; Nomura, M. J. Org. Chem. 1995, 60, 4999.
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33. We have also observed that the addition reaction can be conducted in acetonitrile solvent.
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