Enolate Formation from α-Iodoaldehydes and α-Iodoketones by Means of Allylsilane-Titanium Tetrachloride and Its Application to an Aldol Reaction

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4558-4560

  Maeda, Katsuya ^a   Shinokubo, Hiroshi ^a   Oshima, Koichiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000264684     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980456n     Document Type: Article

References (33)

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2. Mukaiyama, T. Org. React. 1982, 28, 203. Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.4, pp 99-131. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.6, pp 181-238. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.7, pp 239-275. Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.8 pp 277-299. Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.9, pp 301-319.
3. Mukaiyama, T. Org. React. 1982, 28, 203. Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.4, pp 99-131. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.6, pp 181-238. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.7, pp 239-275. Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.8 pp 277-299. Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.9, pp 301-319.
4. Mukaiyama, T. Org. React. 1982, 28, 203. Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.4, pp 99-131. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.6, pp 181-238. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.7, pp 239-275. Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.8 pp 277-299. Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.9, pp 301-319.
5. Mukaiyama, T. Org. React. 1982, 28, 203. Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.4, pp 99-131. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.6, pp 181-238. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.7, pp 239-275. Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.8 pp 277-299. Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.9, pp 301-319.
6. Mukaiyama, T. Org. React. 1982, 28, 203. Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.4, pp 99-131. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.6, pp 181-238. Kim, B. M.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.7, pp 239-275. Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.8 pp 277-299. Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.9, pp 301-319.
7. 3
8. 3
9. 3
10. 3
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13. Yachi, K.; Maeda, K.; Shinokubo, H.; Oshima, K. Tetrahedron Lett. 1997, 38, 5161. Maeda, K.; Shinokubo, H.; Oshima, K. J. Org. Chem. 1997, 62, 6429.
14. 3 in ether. Details are available in the Supporting Information section.
15. (a) Nakamura, E.; Shimada, J.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1983, 24, 3341.
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26. For synthesis of β-hydroxyaldehyde by other methods, see (a) Reduction of β-hydroxyamide: Mukaiyama, T.; Iwasawa, N. Chem. Lett. 1982, 1903. (b) Enzymatic method: Bianchi, D.; Cesti, P.; Golini, P. Tetrahedron 1982, 45, 869.
27. For synthesis of β-hydroxyaldehyde by other methods, see (a) Reduction of β-hydroxyamide: Mukaiyama, T.; Iwasawa, N. Chem. Lett. 1982, 1903. (b) Enzymatic method: Bianchi, D.; Cesti, P.; Golini, P. Tetrahedron 1982, 45, 869.
28. Titanium tetraisopropoxide and titanium tetraphenoxide were not so effective as titanium tetrabutoxide. Although the role of titanium tetrabutoxide is not clear at this stage, we are tempted to assume that the bulky butoxy group on titanium in the aldol adduct β-titanoxyal-dehyde would inhibit the attack of allylsilane on the aldehyde moiety. The protection of the aldehyde group by a bulky aluminum complex from an attack of a nucleophile has been reported, see: Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 777, 9091. Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928. Ooi, T.; Miura, T.; Kondo, Y.; Maruoka, K. Tetrahedron Lett. 1997, 38, 3947.
29. Titanium tetraisopropoxide and titanium tetraphenoxide were not so effective as titanium tetrabutoxide. Although the role of titanium tetrabutoxide is not clear at this stage, we are tempted to assume that the bulky butoxy group on titanium in the aldol adduct β-titanoxyal-dehyde would inhibit the attack of allylsilane on the aldehyde moiety. The protection of the aldehyde group by a bulky aluminum complex from an attack of a nucleophile has been reported, see: Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 777, 9091. Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928. Ooi, T.; Miura, T.; Kondo, Y.; Maruoka, K. Tetrahedron Lett. 1997, 38, 3947.
30. Titanium tetraisopropoxide and titanium tetraphenoxide were not so effective as titanium tetrabutoxide. Although the role of titanium tetrabutoxide is not clear at this stage, we are tempted to assume that the bulky butoxy group on titanium in the aldol adduct β-titanoxyal-dehyde would inhibit the attack of allylsilane on the aldehyde moiety. The protection of the aldehyde group by a bulky aluminum complex from an attack of a nucleophile has been reported, see: Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 777, 9091. Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928. Ooi, T.; Miura, T.; Kondo, Y.; Maruoka, K. Tetrahedron Lett. 1997, 38, 3947.
31. Titanium tetraisopropoxide and titanium tetraphenoxide were not so effective as titanium tetrabutoxide. Although the role of titanium tetrabutoxide is not clear at this stage, we are tempted to assume that the bulky butoxy group on titanium in the aldol adduct β-titanoxyal-dehyde would inhibit the attack of allylsilane on the aldehyde moiety. The protection of the aldehyde group by a bulky aluminum complex from an attack of a nucleophile has been reported, see: Maruoka, K.; Imoto, H.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 4131. Maruoka, K.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1995, 777, 9091. Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928. Ooi, T.; Miura, T.; Kondo, Y.; Maruoka, K. Tetrahedron Lett. 1997, 38, 3947.
32. For a reductive formation of enolate from α-iodoketone with various organometallic compounds, see: Aoki, Y.; Oshima, K.; Utimoto, K. Chem. Lett. 1995, 463.
33. 4 followed by an addition of acetaldehyde.