A selective partial hydrolysis of dimenthyl ester using dry tetrabutylammonium hydroxide

Synlett

Volumn , Issue 1, 1999, Pages 84-86

  Hasegawa, Tomoyuki ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Dimenthyl ester; Half ester; Partial hydrolysis; Tetra butylammonium hydroxide

Indexed keywords

ESTER; TETRABUTYLAMMONIUM;

ARTICLE; CONFORMATIONAL TRANSITION; HYDROLYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS;

EID: 0032940678     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2529     Document Type: Article

References (17)

1. Jones, G.; Raphael, R. A.; Wright, S. J. Chem. Soc., Perkin Trans. 1 1974, 1676; Fischli, A.; Klaus, M.; Mayer, H.; Schönholzer, P.; Rüegg, R. Helv. Chim. Acta. 1975, 58, 564.
2. Jones, G.; Raphael, R. A.; Wright, S. J. Chem. Soc., Perkin Trans. 1 1974, 1676; Fischli, A.; Klaus, M.; Mayer, H.; Schönholzer, P.; Rüegg, R. Helv. Chim. Acta. 1975, 58, 564.
3. Hamanaka, N.; Seko, T.; Miyazaki, T.; Naka, M.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 2399; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 2122.
4. Hamanaka, N.; Seko, T.; Miyazaki, T.; Naka, M.; Furuta, K.; Yamamoto, H. Tetrahedron Lett. 1989, 30, 2399; Ohtani, M.; Matsuura, T.; Watanabe, F.; Narisada, M. J. Org. Chem. 1991, 56, 2122.
5. Furuta, K.; Iwanaga, K.; Yamamoto, H. Tetrahedron Lett. 1986, 37, 4507.
6. Misumi, A.; Iwanaga, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343; Furuta, K.; Iwanaga, K.; Yamamoto, H. Org. Synth. 1989, 67, 76.
7. Misumi, A.; Iwanaga, K.; Furuta, K.; Yamamoto, H. J. Am. Chem. Soc. 1985, 107, 3343; Furuta, K.; Iwanaga, K.; Yamamoto, H. Org. Synth. 1989, 67, 76.
8. Kigoshi, H.; Imamura, Y.; Mizuta, K.; Niwa, H.; Yamada, K. J. Am. Chem. Soc. 1993, 115, 3056.
9. See for discrimination of two carbonyl groups using chiral unsymmetrical fumarates and maleates: Furuta, K.; Hayashi, S.; Miwa, Y.; Yamamoto, H. Tetrahedron Lett. 1987, 28, 5841; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1992, 114, 1089; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
10. See for discrimination of two carbonyl groups using chiral unsymmetrical fumarates and maleates: Furuta, K.; Hayashi, S.; Miwa, Y.; Yamamoto, H. Tetrahedron Lett. 1987, 28, 5841; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1992, 114, 1089; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
11. See for discrimination of two carbonyl groups using chiral unsymmetrical fumarates and maleates: Furuta, K.; Hayashi, S.; Miwa, Y.; Yamamoto, H. Tetrahedron Lett. 1987, 28, 5841; Maruoka, K.; Saito, S.; Yamamoto, H. J. Am. Chem. Soc. 1992, 114, 1089; Maruoka, K.; Akakura, M.; Saito, S.; Ooi, T.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 6153.
12. Hasegawa, T.; Yamamoto, H. Synlett 1998, 882.
13. Roberts, W.; Whiting, M. C. J. Chem. Soc. 1965, 1290.
14. Gassman, P. G.; Schenk, W. N. J. Org. Chem. 1977, 42, 918.
15. 2).
16. Ito, Y. N.; Ariza, X.; Beck, A. K.; Bohác, A.; Ganter, C.; Gawley, R. E.; Kühnle, F. N. M.; Tuleja, J.; Wang, Y. M.; Seebach, D. Helv. Chim. Acta. 1994, 77, 2071.
17. 4: C 71.39; H 9.59. Found: C 71.10; H 9.39.