Effect of calcium reagents on aldol reactions of phenolic enolates with aldehydes in alcohol

Journal of Organic Chemistry

Volumn 61, Issue 20, 1996, Pages 6768-6769

  Saimoto, Hiroyuki ^a   Yoshida, Koji ^a   Murakami, Tetsuya ^a   Morimoto, Minoru ^a   Sashiwa, Hitoshi ^a   Shigemasa, Yoshihiro ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000603443     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961352k     Document Type: Article

References (24)

1. For reviews, see: (a) Grieco, P. A. Aldrichim. Acta 1991, 24, 59. (b) Li, C. J. Chem. Rev. 1993, 93, 2023. (c) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
2. For reviews, see: (a) Grieco, P. A. Aldrichim. Acta 1991, 24, 59. (b) Li, C. J. Chem. Rev. 1993, 93, 2023. (c) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
3. For reviews, see: (a) Grieco, P. A. Aldrichim. Acta 1991, 24, 59. (b) Li, C. J. Chem. Rev. 1993, 93, 2023. (c) Lubineau, A.; Auge, J.; Queneau, Y. Synthesis 1994, 741.
4. Patil, V. J. Tetrahedron Lett. 1996, 37, 1481.
5. (a) Schmid, W.; Whitesides, G. M. J. Am. Chem. Soc. 1991, 113, 6674.
6. (b) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256.
7. Denis, C.; Laignel, B.; Plusquellec, D.; Le Marouille, J.-Y.; Botrel, A. Tetrahedron Lett. 1996, 37, 53.
8. Shigemasa, Y.; Yokoyama, K.; Sashiwa, H.; Saimoto, H. Tetrahedron Lett. 1994, 35, 1263.
9. Saimoto, H.; Yatani, S.; Sashiwa, H.; Shigemasa, Y. Tetrahedron Lett. 1995, 36, 937.
10. 2O (59 mg, 0.4 mmol) in 0.4 M KOH methanol solution (2 mL) for 24 h at 0 °C. After acidification with 1 M HCl, extractive workup followed by purification by preparative TLC (benzene-EtOAc 10:1, developed twice) afforded 2b (131 mg) along with 1 (27 mg).
11. Different regioselectivity in the reaction of resorcinols with aldehydes and formation of resins: (a) Högberg, A. G. S. J. Am. Chem. Soc. 1980, 102, 6046. (b) Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305. (c) Konishi, H.; Ohata, K.; Morikawa, O.; Kobayashi, K. J. Chem. Soc., Chem. Commun. 1995, 309. (d) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, Great Britain, 1989; and references cited therein.
12. Different regioselectivity in the reaction of resorcinols with aldehydes and formation of resins: (a) Högberg, A. G. S. J. Am. Chem. Soc. 1980, 102, 6046. (b) Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305. (c) Konishi, H.; Ohata, K.; Morikawa, O.; Kobayashi, K. J. Chem. Soc., Chem. Commun. 1995, 309. (d) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, Great Britain, 1989; and references cited therein.
13. Different regioselectivity in the reaction of resorcinols with aldehydes and formation of resins: (a) Högberg, A. G. S. J. Am. Chem. Soc. 1980, 102, 6046. (b) Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305. (c) Konishi, H.; Ohata, K.; Morikawa, O.; Kobayashi, K. J. Chem. Soc., Chem. Commun. 1995, 309. (d) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, Great Britain, 1989; and references cited therein.
14. Different regioselectivity in the reaction of resorcinols with aldehydes and formation of resins: (a) Högberg, A. G. S. J. Am. Chem. Soc. 1980, 102, 6046. (b) Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J. C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305. (c) Konishi, H.; Ohata, K.; Morikawa, O.; Kobayashi, K. J. Chem. Soc., Chem. Commun. 1995, 309. (d) Gutsche, C. D. Calixarenes; The Royal Society of Chemistry: Cambridge, Great Britain, 1989; and references cited therein.
15. Mon, K.; Kamada, A.; Mori, H. Liebigs Ann. Chem. 1989, 303.
16. In the case of α,β-unsaturated aldehydes, small amounts of side products of type 4 were formed.
17. Leading references of the synthesis of naturally occurring 2H-chromenes: (a) Cardillo, G.; Cricchio, R.; Merlini, L. Tetrahedron 1968, 24, 4825. (b) Crombie, L.; Crombie, W. M. L.; Forbes, R.; Whitaker, A. J. Chem. Res., Miniprint 1977, 1301. (c) Mohamed, S. E. N.; Thomas, P.; Whiting, D. A. J. Chem. Soc., Perkin Trans, 1 1987, 431. (d) Iyer, M. R.; Trivedi, G. K. J. Nat. Prod. 1993, 56, 268. (e) Yamaguchi, S.; Shouji, N.; Kuroda, K. Bull. Chem. Soc. Jpn. 1995, 68, 305.
18. Leading references of the synthesis of naturally occurring 2H-chromenes: (a) Cardillo, G.; Cricchio, R.; Merlini, L. Tetrahedron 1968, 24, 4825. (b) Crombie, L.; Crombie, W. M. L.; Forbes, R.; Whitaker, A. J. Chem. Res., Miniprint 1977, 1301. (c) Mohamed, S. E. N.; Thomas, P.; Whiting, D. A. J. Chem. Soc., Perkin Trans, 1 1987, 431. (d) Iyer, M. R.; Trivedi, G. K. J. Nat. Prod. 1993, 56, 268. (e) Yamaguchi, S.; Shouji, N.; Kuroda, K. Bull. Chem. Soc. Jpn. 1995, 68, 305.
19. Leading references of the synthesis of naturally occurring 2H-chromenes: (a) Cardillo, G.; Cricchio, R.; Merlini, L. Tetrahedron 1968, 24, 4825. (b) Crombie, L.; Crombie, W. M. L.; Forbes, R.; Whitaker, A. J. Chem. Res., Miniprint 1977, 1301. (c) Mohamed, S. E. N.; Thomas, P.; Whiting, D. A. J. Chem. Soc., Perkin Trans, 1 1987, 431. (d) Iyer, M. R.; Trivedi, G. K. J. Nat. Prod. 1993, 56, 268. (e) Yamaguchi, S.; Shouji, N.; Kuroda, K. Bull. Chem. Soc. Jpn. 1995, 68, 305.
20. Leading references of the synthesis of naturally occurring 2H-chromenes: (a) Cardillo, G.; Cricchio, R.; Merlini, L. Tetrahedron 1968, 24, 4825. (b) Crombie, L.; Crombie, W. M. L.; Forbes, R.; Whitaker, A. J. Chem. Res., Miniprint 1977, 1301. (c) Mohamed, S. E. N.; Thomas, P.; Whiting, D. A. J. Chem. Soc., Perkin Trans, 1 1987, 431. (d) Iyer, M. R.; Trivedi, G. K. J. Nat. Prod. 1993, 56, 268. (e) Yamaguchi, S.; Shouji, N.; Kuroda, K. Bull. Chem. Soc. Jpn. 1995, 68, 305.
21. Leading references of the synthesis of naturally occurring 2H-chromenes: (a) Cardillo, G.; Cricchio, R.; Merlini, L. Tetrahedron 1968, 24, 4825. (b) Crombie, L.; Crombie, W. M. L.; Forbes, R.; Whitaker, A. J. Chem. Res., Miniprint 1977, 1301. (c) Mohamed, S. E. N.; Thomas, P.; Whiting, D. A. J. Chem. Soc., Perkin Trans, 1 1987, 431. (d) Iyer, M. R.; Trivedi, G. K. J. Nat. Prod. 1993, 56, 268. (e) Yamaguchi, S.; Shouji, N.; Kuroda, K. Bull. Chem. Soc. Jpn. 1995, 68, 305.
22. Shoyama, Y.; Hirano, H.; Makino, H.; Umekita, N.; Nishioka, I. Chem. Pharm. Bull. 1977, 25, 2306.
23. Different regioselectivity was reported on the reaction of 5-methylresorcinol with cinnamaldehyde: Sartori, G.; Casiraghi, G.; Bolzoni, L.; Casnati, G. J. Org. Chem. 1979, 44, 803.
24. Previously 19 was prepared from 20: Shoyama, Y.; Hirano, H.; Nishioka, I. J. Labelled Compd. Radiopharm. 1978, 14, 835. (Matrix Presented)