Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Transformation of Carboxylic Acids and Their Derivatives into Aldehydes by Lithium Tris(dialkylamino)aluminum Hydrides

  • Cha Jin Soon (Department of Chemistry, Yeungnam University)
  • Published : 1992.12.20
Download PDF
⟨ Previous Next ⟩

Abstract

A systematic study of the partial reduction of carboxylic acids and their derivatives to the corresponding aldehydes with lithium tris(dialkylamino)aluminum hydrides under practical conditions has been carried out. The diethylaminosubstituted derivative of lithium aluminum hydride, lithium tris(diethylamino)aluminum hydride (LTDEA), shows quite general applicability in the conversion of carboxylic acids, carboxylic esters, and primary carboxamides to the corresponding aldehydes. Lithium tripiperidinoaluminum hydride (LTPDA) also appears to be a reagent of choice for such partial transformation of primary carboxamides. In additioin, both LTDEA and LTPDA reduce tertiary carboxyamides to aldehydes in high yields. Finally, lithium tris(dihexylamino)aluminum hydride (LTDHA) is capable of achieving the chemoselective reduction of aromatic nitriles to aldehydes in the presence of aliphatic nitriles under practical conditions.

Keywords

References

  1. Compendium of Organic Synthetic Methods v.1;2;3 I. T. Harrison;D. Harrison
  2. Org. React. v.8 E. Mosettig
  3. Org. React. v.34;36 J. Malek
  4. J. Am. Chem. Soc. v.69 A. E. Finhalt;A. C. Bond;H. I. Schlesinger
  5. Tetrahedron Lett. L. I. Zakharkin;I. M. Khorlina
  6. J. Org. Chem. v.31 P. M. Weissman;H. C. Brown
  7. Synthesis R. Kanazawa;T. Tokoroyama
  8. J. Am. Chem. Soc. v.86 H. C. Brown;A. Tsukamoto
  9. J. Am. Chem. Soc. v.80 H. C. Brown;B. C. Subba Rao
  10. Tetradhedron Lett. v.9 H. C. Brown;C. J. Shoat;C. P. Garg
  11. J. Am. Chem. Soc. v.86 H. C. Brown;C. P. Garg
  12. Bull. Korean Chem. Soc. v.12 J. S. Cha;S. E. Lee;H. S. Lee
  13. Tetrahedron Lett. v.32 J. S. Cha;J. C. Lee;S. E. Lee;J. M. Kim;O. O. Kwon;H. S. Lee;S. J. Min
  14. Bull. Korean Chem. Soc. v.12 J. S. Cha;J. C. Lee;S. E. Lee;H. S. Lee
  15. Org. Prep. Proced. Int. v.24 J. S. Cha;J. C. Lee;H. S. Lee
  16. Org. Prep. Proced. Int. v.24 J. S. Cha;S. E. Lee;H. S. Lee
  17. Bull. Korean Chem. Soc. v.13 J. S. Cha;S. E. Lee;H. S. Lee;J. C. Lee;J. M. Kim;O. O. Kwon;S. J. Min
  18. Org. Prep. Proced. Int. v.24 J. S. Cha;S. J. Min;J. C. Lee;S. E. Lee;H. S. Lee
  19. Tetrachedron Lett. v.28 J. S. Cha;J. E. Kim;S. Y. Oh;J. D. Kim
  20. Bull. Korean Chem. Soc. v.9 J. S. Cha;S. Y. Oh;K. W. Lee;M. S. Yoon;J. C. Lee;J. E. Kim
  21. Tetrahedron Lett. v.28 J. S. Cha;J. E. Kim;M. S. Yoon;Y. S. Kim
  22. Bull. Korean Chem. Soc. v.11 J. S. Cha;J. C. Lee;M. S. Yoon;J. B. Seo;J. M. Kim
  23. J. Org. Chem. v.52 H. C. Brown;J. S. Cha;B. Nazer;N. M. Yoon
  24. J. Org. Chem. v.31 P. M. Weissman;H. C. Brown
  25. Tetrahedron Lett. L. I. Zakharkin;I. M. Khorlina
  26. Iza. Akad. Nauk. SSSR, Ser. Khim L. I. Zakharkin;I. M. Khorlina
  27. Chemistry Lett. M .Muraki;T. Mukaiyama
  28. J. Am. Chem. Soc. v.83 H. C. Brown;A. Tsukamoto
  29. Ann. v.577 G. Witting;P. Hornberger
  30. Angew. Chem. v.64 F. Weygand;G. Eberhardt
  31. Angew. Chem. v.65 F. Weygand;G. Eberhardt;H. Linden;F. Schafter;I. Eigen
  32. Angew. Chem. v.66 F. Weygand;H. Linden
  33. Ber. v.88 F. Weygand;R. Mitgau
  34. Chem. Ber. v.92 F. Weygand;J. Bestmann
  35. Angew. Chem. v.70 W. Ried;F. J. Konigstein
  36. Ann. v.640 W. Ried;P. Pfaeender
  37. Ann. v.654 H. A. Staab;H. Braunling
  38. Synthesis J. A. Fehrentz;B. Castro
  39. Tetrahedron Lett. V. Bazant;M. Capka;M. Cerny;V. Chavalosky;K. Kocholoefl;M. Krasus;J. Malek
  40. Tetrahedron v.29 N. S. Ramegowda;M. N. Modi;A. K. Koul;J. M. Bora;C. K. Narang;N. K. Mathur
  41. J. Chem. Soc. Perkin Transaction v.1 Y. Nagao;K. Kwabata;K. Seno;E. Fujita
  42. Chemistry Lett. T. Izawa;T. Mukaiyama
  43. Bull. Chem. Soc. Jpn. v.52 T. Izawa;T. Mukaiyama
  44. J. Am. Chem. Soc. v.86 H. C. Brown;A. Tsukamoto
  45. J. Am. Chem. Soc. v.81 H. C. Brown;A. Tsukamoto
  46. Tetrahedron v.25 I. I. Zakharkin;D. N. Maslin;V. V. Gavrilenko
  47. Chemistry Lett. M .Muraki;T. Mukaiyama
  48. J. Chem. Soc. v.127 E. Stephen
  49. Angew. Chem. v.68 G. Hesse;R. Schrodel
  50. Ann. v.607
  51. Tetrahedron Lett. v.9 H. C. Brown;C. J. Schoaf;C. P. Grag
  52. J. Chem. Educ. v.38 H. C. Brown
  53. J. Am. Chem. Soc. v.86 H. C. Brown;C. P. Garg
  54. Bull. Soc. Chim. Fr. v.12 D. de Peretti;T. Strzalko-Bottin;J. Seydenpenne
  55. Dokl. Akad. Nauk SSSR v.116 L. I. Zakharkin;I. M .Kohrlina
  56. J. Org. Chem. v.35 J. A. Marshall;N. H. Andersen;P. C. Johnson
  57. J. Org. Chem. v.37 R. V. Stevens;L. E. DuPree, Jr.;P. L. Loewenstein
  58. Tetrahedron Lett. M. P. L. Caton;E. C. J. Coffee;G. L. Waktkins
  59. Bull. Korean Chem. Soc. v.7 N. M. Yoon;S. K. Kim;Y. S. Gyong
  60. Gazz. Chim. Ital v.85 S. Peitra;C. Trinchera
  61. Compt. Rend. v.252;254 A. Gaiffe;R. Pallaud
  62. Angew. Chim. v.67 H. Plieninger;G. Werst
  63. Chem. Ber. v.88
  64. J. Org. Chem. v.27 J. N. Coker;W. L. Kohlhase;M. Fields;A. O. Rogers;M. A. Stevens
  65. J. Chem. Soc. B. Staskun;O. G. Backeberg
  66. J. Chem. Soc. T. van Es;B. Staskun
  67. Org. Syn. v.51
  68. Chem. Comm. J. L. Fry
  69. J. Org. Chem. v.46 J. L. Fry;R. A. Ott
  70. Bull. Korean Chem. Soc. v.8 J. S. Cha;S. Y. Oh;J. E. Kim
  71. Tetrahedron Lett. v.30 J. S. Cha;M. S. Yoon
  72. Organic Syntheses, Coll v.4 A. C. Cope;E. Ciganek

Cited by

  1. ChemInform Abstract: Transformation of Carboxylic Acids and Their Derivatives into Aldehydes by Lithium Tris(dialkylamino)aluminum Hydrides. vol.24, pp.24, 1993, https://doi.org/10.1002/chin.199324104
  2. Pyrimidine derivatives XII. A convenient preparation of 6-formylpyrimidinedione and 2- and 3-formylpyridine derivatives from corresponding nitrooxymethyl derivatives vol.31, pp.6, 1994, https://doi.org/10.1002/jhet.5570310654
  3. 2-Amino-2-Deoxytetrose Derivatives. 2. Preparation from d-Glyceraldehyde Acetonide: A Reinvestigation vol.14, pp.9, 1992, https://doi.org/10.1080/07328309508005414
  4. XIIth international symposium on radiopharmaceutical chemistry: Abstracts and programme vol.40, pp.None, 1992, https://doi.org/10.1002/jlcr.2580400401
  5. Controlled reduction of tertiary amides to the corresponding aldehydes or amines using dialkylboranes vol.38, pp.10, 1997, https://doi.org/10.1016/s0040-4039(97)00179-2
  6. Solid phase‐supported reaction of N.C.A. H11CN with arabinose: a simplified automated synthesis of D‐[1‐11C]glucose vol.41, pp.4, 1992, https://doi.org/10.1002/(sici)1099-1344(199804)41:4<287::aid-jlcr80>3.0.co;2-5
  7. Selective Conversion of Aromatic Nitriles to Aldehydes by Lithium N,N'-Dimethylethylenediaminoaluminum Hydride vol.23, pp.12, 1992, https://doi.org/10.5012/bkcs.2002.23.12.1697
  8. Conversion of Carboxylic Acids to Aldehydes with Cyclic Dialkyldiaminoaluminum Hydrides vol.23, pp.9, 1992, https://doi.org/10.5012/bkcs.2002.23.9.1340
  9. Selective Reduction of Aromatic Nitriles to Aldehydes by Lithium Diisobutylpiperidinohydroaluminate (LDBPA) vol.27, pp.1, 1992, https://doi.org/10.5012/bkcs.2006.27.1.121
  10. Partial and Chemoselective Reduction of Nitriles with Metal Diisobutyl-t-butoxyaluminum Hydrides vol.29, pp.11, 1992, https://doi.org/10.5012/bkcs.2008.29.11.2303
  11. Reaction of lithium tris(tert-butylthiolato)hydridoaluminate with selected organic compounds containing representative functional groups vol.65, pp.1, 2009, https://doi.org/10.1007/s10847-009-9628-4
  12. A New Method of Partial and Chemoselective Reduction of Nitriles to Aldehydes by Lithium Diisobutyl-iso-propoxyaluminum Hydride (LDBIPA) vol.31, pp.2, 1992, https://doi.org/10.5012/bkcs.2010.31.02.473
  13. Thirty Six Years of Research on the Selective Reduction and Hydroboration vol.32, pp.6, 1992, https://doi.org/10.5012/bkcs.2011.32.6.1808