Diarylborinic acids as efficient catalysts for selective dehydration of aldols

Synlett

Volumn , Issue 5, 1997, Pages 597-599

  Ishihara, Kazuaki ^a   Kurihara, Hideki ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000553303     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-3207     Document Type: Article

References (16)

1. (a) Ishihara, K.; Hanaki, N.; Yamamoto, H. Synlett 1993, 577.
2. (b) Ishihara, K.; Funahashi, M.; Hanaki, N.; Miyata, M.; Yamamoto, H. Synlett 1994, 963.
3. (c) Ishihara, K.; Hanaki, N.; Funahashi, M.; Miyata, M.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 1721.
4. (d) Ishihara, K.; Hanaki, N.; Yamamoto, H. Synlett 1996, 721.
5. Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440.
6. 4
7. Chambers, R. D.; Chivers, T. J. Chem. Soc. 1965, 3933.
8. 12BO: C, 42.33; H, 1.60. Found: C, 42.20; H, 1.47.
9. For 3,4,5-trifluorobenzeneboronic acid as an amidation catalyst, see: Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4196.
10. Dehydration of the trimethylsilyl ether of 4 proceeded relatively slowly. The dehydration of the silyl ether is believed to proceed via hydrolysis, based on the experimental finding that small amounts of 4 were observed during the dehydration.
11. For other useful methods for the dehydration of β-hydroxy carbonyl compounds, see: (a) Corey, E. J.; Andersen, N. H.; Carlson, R. M.; Paust, J.; Vedejs, E.; Vlattas, I.; Winter, R. E. K. J. Am. Chem. Soc. 1968, 90, 3245.
12. (b) Stork, G.; Shiner, C. S.; Winkler, J. D. J. Am. Chem. Soc. 1982, 104, 310. In most cases, β-hydroxy carbonyl compounds are dehydrated under severe conditions such as heating in the presence of strong acids or bases.
13. 3) (Formula Presented)
14. Matter, U. E.; Pascual, C.; Pretsch, E.; Pross, A.; Simon, W.; Sternhell, S. Tetrahedron 1969, 25, 691.
15. It was ascertained by control experiments that dehydrations of syn- and anti-isomeric aldol mixtures catalyzed by TsOH were not substrate- diastereoselective.
16. Ishihara, K.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 3049.