Regioselective alkylation of 1-alkoxy-3-phenylseleno-1-alkenes

Synlett

Volumn , Issue 5, 1999, Pages 611-613

  Nishiyama, Yutaka ^a   Kishimoto, Yoshihiro ^a   Itoh, Kazuyoshi ^a   Sonoda, Noboru ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

1 alkoxy 3 phenylseleno 1 alkenes; Alkyl halides; Alkylation; LDA; Regioselective

Indexed keywords

ALKENE DERIVATIVE; ORGANOLITHIUM COMPOUND;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0032937848     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2683     Document Type: Article

References (21)

1. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
2. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
3. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
4. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
5. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
6. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
7. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
8. Reich, H. J. J. Org. Chem. 1975, 40, 2570. Raucher, S.; Koolpe, G. A. J. Org. Chem. 1978, 43, 3794. Binns, M. B.; Haynes, R. K.; Houston, T. L.; Jackson, W. R. Tetrahedron Lett., 1980, 21, 573. Binns, M. B.; Clark, M. C.; Willis, Jr. W. W. J. J. Org. Chem. 1982, 47, 1618. Yamamoto, Y.; Saito, Y.; Maruyama, K. Tetrahedron Lett. 1982, 23, 4597. Yamamoto, Y.; Saito, Y.; Maruyama, K. J. Org. Chem. 1983, 48, 5408. Yamamoto, Y.; Yatagai, H.; Saito, Y.; Maruyama, K. J. Org. Chem. 1984, 49, 1096. Clarembeau, M.; Krief, A. Tetrahedron Lett., 1984, 25, 3629 and references therein.
9. Nishiyama, Y.; Asano, T.; Kishimoto, Y.; Itoh, K.; Ishii, Y. Tetrahedron Lett., Tetrahedron Lett., 1998, 39, 8635.
10. 4, its concentration and purification by column chromatography on silica gel (n-hexane:diethyl ether = 160:1) yielded 1-ethoxy-3-phenyl-seleno-1-heptene in 82% (0.82 mmol, 250 mg) as a yellow oil.
11. It was reported that the reaction of phenylseleno-substituted allyllithiums with carbonyl compounds afford the corresponding γ-alkylated product, predominantly. See: Clive, D. L. J. Tetrahedron 1978, 34, 1049 and references therein.
12. Even when the alkylation with benzaldehyde was carried out at -100 °C, γ-alkylated product was not formed at all.
13. To the best of our knowledge, there are no reports on the alkylation of lithium anions of the α-alkyl substituted allyl phenylselenidc due to the difficulty in the clear deprotonation of α-methylallyl phenylselenide. See: Reich, H. J. J. Org. Chem. 1975, 40, 2570.
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15. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press; Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds; Vol. 1 and 2:1986. Krief, A.; Hevesi, L. In Organoselenium Chemistry; Vol. 1: Springer Verlag: Berlin, 1988. Krief, A. In Comprehensive Organic Synthesis; Vol. 3; Trost, B. M., Eds.; Pergamon Press; Oxford, 1991; p 85-192 and references cited therein.
16. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press; Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds; Vol. 1 and 2:1986. Krief, A.; Hevesi, L. In Organoselenium Chemistry; Vol. 1: Springer Verlag: Berlin, 1988. Krief, A. In Comprehensive Organic Synthesis; Vol. 3; Trost, B. M., Eds.; Pergamon Press; Oxford, 1991; p 85-192 and references cited therein.
17. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press; Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds; Vol. 1 and 2:1986. Krief, A.; Hevesi, L. In Organoselenium Chemistry; Vol. 1: Springer Verlag: Berlin, 1988. Krief, A. In Comprehensive Organic Synthesis; Vol. 3; Trost, B. M., Eds.; Pergamon Press; Oxford, 1991; p 85-192 and references cited therein.
18. Paulmier, C. In Selenium Reagents and Intermediates in Organic Synthesis; Pergamon Press; Oxford, 1986. Patai, S.; Rappoport, Z. In The Chemistry of Organic Selenium and Tellurium Compounds; Vol. 1 and 2:1986. Krief, A.; Hevesi, L. In Organoselenium Chemistry; Vol. 1: Springer Verlag: Berlin, 1988. Krief, A. In Comprehensive Organic Synthesis; Vol. 3; Trost, B. M., Eds.; Pergamon Press; Oxford, 1991; p 85-192 and references cited therein.
19. It is known that the reaction of electrophiles with lithium salt generated from the deprotonation of the allyl ethers by s-BuLi proceeded high regiosclectivity to give the corresponding vinyl ethers in good yields. In this manuscript, they suggested that the chelation between the lithium cation and oxygen atom at the ether group plays an important role in the high regioselectivity. See: Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535. Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560. Still, W. C.; Macdonald, T. L. J. Org. Chem. 1976, 41, 3620.
20. It is known that the reaction of electrophiles with lithium salt generated from the deprotonation of the allyl ethers by s-BuLi proceeded high regiosclectivity to give the corresponding vinyl ethers in good yields. In this manuscript, they suggested that the chelation between the lithium cation and oxygen atom at the ether group plays an important role in the high regioselectivity. See: Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535. Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560. Still, W. C.; Macdonald, T. L. J. Org. Chem. 1976, 41, 3620.
21. It is known that the reaction of electrophiles with lithium salt generated from the deprotonation of the allyl ethers by s-BuLi proceeded high regiosclectivity to give the corresponding vinyl ethers in good yields. In this manuscript, they suggested that the chelation between the lithium cation and oxygen atom at the ether group plays an important role in the high regioselectivity. See: Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535. Evans, D. A.; Andrews, G. C.; Buckwalter, B. J. Am. Chem. Soc. 1974, 96, 5560. Still, W. C.; Macdonald, T. L. J. Org. Chem. 1976, 41, 3620.