Practical Synthesis of (±)-α-Tocopherol. Trifluoromethanesulfonimide as an Extremely Active Brønsted Acid Catalyst for the Condensation of Trimethylhydroquinone with Isophytol

Synlett

Volumn 1996, Issue 11, 1996, Pages 1045-1046

  Ishihara, Kazuaki ^a   Kubota, Manabu ^a   Yamamoto, Hisashi ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000248916     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5672     Document Type: Article

References (12)

1. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413, 6639 (corrections); Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4560.
2. Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Am. Chem. Soc. 1995, 117, 4413, 6639 (corrections); Ishihara, K.; Kubota, M.; Kurihara, H.; Yamamoto, H. J. Org. Chem. 1996, 61, 4560.
3. Matsui, M.; Karibe, N.; Hayashi, K.; Yamamoto, H. Bull. Chem. Soc. Jpn. 1995, 68, 3569.
4. 3, see: Ishihara, K.; Kubota, M.; Yamamoto, H. Synlett 1996, 265.
5. 3, see: Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett 1996, 839.
6. Very recently, bis(fluorosulfuryl)imide was reported to be an effective Brønsted acid catalyst for the addition of allyltrimethylsilane to carbonyl compounds: Kaur, G.; Manju, K.; Trehan, S. J. Chem. Soc., Chem. Commun. 1996, 581.
7. Ichikawa, T.; Kato, T. Bull. Chem. Soc. Jpn. 1968, 41, 1224; Mayer, H.; Isler, O. Methods in Enzymology, ed. Colowick, S. P.; Kaplan, N. O. Academic Press, New York, 1971, Vol. XVIIIC, p. 241-348; Schudel, P.; Mayer, H.; Isler, O. The Vitamins, ed. Sebrell, W. H.; Harris, R. S. Academic Press, New York, 1972, Vol. V, p. 168-218; Ismail, F. M. D.; Hilton, M. J.; Stefinovic, M. Tetrahedron Lett. 1992, 33, 3795.
8. Ichikawa, T.; Kato, T. Bull. Chem. Soc. Jpn. 1968, 41, 1224; Mayer, H.; Isler, O. Methods in Enzymology, ed. Colowick, S. P.; Kaplan, N. O. Academic Press, New York, 1971, Vol. XVIIIC, p. 241-348; Schudel, P.; Mayer, H.; Isler, O. The Vitamins, ed. Sebrell, W. H.; Harris, R. S. Academic Press, New York, 1972, Vol. V, p. 168-218; Ismail, F. M. D.; Hilton, M. J.; Stefinovic, M. Tetrahedron Lett. 1992, 33, 3795.
9. Ichikawa, T.; Kato, T. Bull. Chem. Soc. Jpn. 1968, 41, 1224; Mayer, H.; Isler, O. Methods in Enzymology, ed. Colowick, S. P.; Kaplan, N. O. Academic Press, New York, 1971, Vol. XVIIIC, p. 241-348; Schudel, P.; Mayer, H.; Isler, O. The Vitamins, ed. Sebrell, W. H.; Harris, R. S. Academic Press, New York, 1972, Vol. V, p. 168-218; Ismail, F. M. D.; Hilton, M. J.; Stefinovic, M. Tetrahedron Lett. 1992, 33, 3795.
10. Ichikawa, T.; Kato, T. Bull. Chem. Soc. Jpn. 1968, 41, 1224; Mayer, H.; Isler, O. Methods in Enzymology, ed. Colowick, S. P.; Kaplan, N. O. Academic Press, New York, 1971, Vol. XVIIIC, p. 241-348; Schudel, P.; Mayer, H.; Isler, O. The Vitamins, ed. Sebrell, W. H.; Harris, R. S. Academic Press, New York, 1972, Vol. V, p. 168-218; Ismail, F. M. D.; Hilton, M. J.; Stefinovic, M. Tetrahedron Lett. 1992, 33, 3795.
11. Triflimide is a stronger Brønsted acid than triflic acid. Koppel, I. A.; Taft, R. W.; Anvia, F.; Zhu, S.-Z.; Hu, L.-Q.; Sung, K.-S.; DesMarteau, D. D.; Yagupolskii, L. M.; Yagupolskii, Y. L.; Ignat'ev, N. V.; Kondratenko, N. V.; Volkonskii, A. Y.; Vlasov, V. M.; Notario, R.; Maria, P.-C. J. Am. Chem. Soc. 1994, 116, 3047.
12. 1 was used after washing with ether and hexane.