Liquid crystal control of regio- and diastereoselectivity in the acid-catalyzed elimination of alkyl phosphates to alkenes

Tetrahedron Letters

Volumn 38, Issue 50, 1997, Pages 8731-8734

  Fukunaga, Kenji ^a   Kansui, Hisao ^a   Taniguchi, Tomoko ^a   Kunieda, Takehisa ^a  

^a KUMAMOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHATE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; LIQUID CRYSTAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030834780     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10321-5     Document Type: Article

References (19)

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3. (c) Maria, P. D.; Lodi, A,; Samori, B.; Rustichelli, F.; Torquati, G. J. Am. Chem. Soc. 1984, 106, 653.
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6. (a) Hiraoka, S.; Yoshida, T.; Kansui, H.; Kunieda, T. Tetrahedron Lett. 1992, 33, 4341.
7. (b) Kansui, H.; Kunieda, T. Tetrahedron Lett. 1995, 36, 5899.
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9. Similar type of elimination with AgOTf was reported. Simagaki, M.; Fujieda, Y.; Kimura, T.; Nakata, T. Tetrahedron Lett. 1995, 36, 719.
10. Neubert, M. E.; Ferrato, J. P.; Carpenter, R. E. Mol. Cryst. Liq. Cryst. 1979, 53, 229.
11. Billard, P. J.; Mamlok, E. L. Mol. Cryst. Liq. Cryst. 1978, 41, 217.
12. Compound 2 : δ 5.48 (m, 1H). Compound 3 : δ 5.20-5.24 (m, 1H). (a) Nakagawa, K.; Sawai, M.; Ishii, Y.; Ogawa, M. Bull. Chem. Soc. Jpn. 1977, 50, 2487.
13. (b) Posner, G. H.; Shulman-Roskes, E. M.; Oh, C. H.; Carry, J. C.; Green, J. V.; Clark, A. B.; Dai, H.; Anjeh, T. E. N. Tetrahedron Lett. 1991, 32, 6489.
14. Acidic treatment of 1 and 4 in nematic PCCA solvent resulted in a 13 : 1 ratio of 2 and 3, while the isotropic reactions in CCA gave the ratio of 9-10 : 1 under the identical conditions.
15. Compound 6a : δ 5.59 (m, 2H). Compound 7a : δ 5.27-5.29 (m, 2H). (a) Douglas, G. H.; Ellington, P. S.; Meakins, G. D.; Swindells, R. J. Chem. Soc. 1959, 1720.
16. (b) McKenna, J.; Norymberski, J. K.; Stubbs, R. D. J. Chem. Soc. 1959, 2502.
17. (c) Angyal, S. J.; Nicholls, R. G.; Pinhey, J. T. Aust. J. Chem. 1979, 32, 2433.
18. Compound 6b : δ 5.49 (m, 2H). Compound 7b : δ 5.31-5.36 (m, 1H), δ 5.62-5.69 (m, 1H). (a) Davis, B. R.; Woodgate, P. D. J. Chem. Soc. 1966, 2006.
19. (b) Abe, K.; Satoh, J. Y. Bull. Chem. Soc. Jpn. 1978, 51, 941.