Selective synthesis of 1-alkoxy-3-phenylseleno-1-alkenes and 3- phenylselenoalkanals by the reaction of diisobutylaluminum phenylselenolate with α,β-unsaturated acetals

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8685-8686

  Nishiyama, Yutaka ^a   Asano, Tomoyuki ^a   Kishimoto, Yoshihiro ^a   Itoh, Kazuyoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALKENE; DIISOBUTYLALUMINUM PHENYLSELENOLATE; HYDROCHLORIC ACID; ORGANOSELENIUM DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ARTICLE; HYDROLYSIS; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0032548039     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01898-X     Document Type: Article

References (15)

1. 1) a) A. Krief and L. Hevesi, in "Organoselenium Chemistry" Springer Verlag, Berlin (1988), Vol. 1;
2. b)C. Paulmier, in "Selenium Reagents and Intermediates in Organic Synthesis," Pergamon Press, Oxford, (1986);
3. c) S. Patai and Z. Rappoport, in "The Chemistry of Organic Selenium and Tellurium Compounds" Vol. 1 and 2, (1986) and references cited therein.
4. 2) The synthetic applications of organoselenium compounds having Se-Al bond: a) M. J. Dahdoub, T. M. Cassol, A. C. F. Batista, Tetrahedron Lett. 1996, 37, 9005.
5. b) T. Inoue, T. Takeda, N. Kamhe, A. Ogawa, I. Ryu, N. Sonoda, J. Org. Chem. 1994, 59, 5824.
6. c) Y. Nishiyama, S. Nakata, S. Hamanaka, Chem. Lett. 1991, 1775.
7. d) K. Maruoka, H. Yamamoto, Angew. Chem. Int. Ed. Engl. 1985, 25, 668.
8. e) B. A. McKittrick, B. Gamem, J. Org. Chem. 1985, 50, 5897.
9. f) K. Maruoka, T. Miyazaki, M. Ando, Y. Matsumura, S. Sakane, K. Hattori, H. Yamamoto, J. Am. Chem. Soc. 1983, 105, 2831.
10. g) A. P. Kozikowski, A. Ames, J. Org. Chem. 1978, 43, 2735.
11. 3) For recent reviews of the utilization of compounds having Se-B and Se-Si; sec L. A. Paquette Ed. in "Encyclopedia of Reagents for Organic Synthesis" John Wiley & Sons Vol. 1-6 (1996).
12. 4) For examples of organic syntheses using selenium compounds having Se-Sn bond; Y. Nishiyama, H. Ohashi, K. Itoh, N. Sonoda, Chem. Lett. 1998,115 and references cited therein.
13. 4, The solvent was removed under reduced pressure, and the resulting oil was isolated by column chromatography on silica gel to give the corresponding l-alkoxy-3-phenylseleno-l-alkenes or 3-phenylselenoalkanals.
14. 6) When the reaction of α,β-unsaturated aldehyde with 1 was carried out, side reactions took place to afford complex mixtures.
15. 3Al) proceeded smoothly to yield 1,4-adduct preferentially, the reason of high regioselectivity was not disclosed on this manuscript, see: J. Fujiwara, Y. Fukutani, M. Hasegawa, K. Maruoka, H. Yamamoto, J. Am. Chem. Soc. 1984, 106, 5004.