Lewis acid mediated selective chalcogenalkylation of silyl enol ethers with [O,S]-acetals

Synthesis

Volumn , Issue 4, 1999, Pages 562-564

  Braga, Antonio L ^a   Dornelles, Luciano ^a   Silveira, Claudio C ^a   Wessjohann, Ludger A ^b,c  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b UNIVERSITY OF MUNICH   (Germany)

^c VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Lewis acid; Monothioacetal; Silyl enol ether; chalcogeno ketone

Indexed keywords

ACETAL DERIVATIVE; SILANE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0032917717     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3429     Document Type: Article

References (20)

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9. Similar reactions using others chalcogcn-stabilized carbenium ions have been described: [oxygen] Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.* Saraswathy, V. G.; Sankararaman, N. J. Chem. Soc., Perkin Trans. I 1996, 29.; [sulfur]: Paterson, I. Tetrahedron, 1988, 44, 4207.* Takeda, T.; Sugi, S.; Nakayama, A.; Suzuki, Y.; Fujiwara, T. Chem. Lett. 1992, 819. [selenium]: Nsunda, K. M.; Hevesi, L. Tetrahedron Lett. 1984, 25, 4441. Comasseto, J. V.; Silveira, C. C. Synth. Commun. 1986, 16, 1167.
10. Similar reactions using others chalcogcn-stabilized carbenium ions have been described: [oxygen] Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.* Saraswathy, V. G.; Sankararaman, N. J. Chem. Soc., Perkin Trans. I 1996, 29.; [sulfur]: Paterson, I. Tetrahedron, 1988, 44, 4207.* Takeda, T.; Sugi, S.; Nakayama, A.; Suzuki, Y.; Fujiwara, T. Chem. Lett. 1992, 819. [selenium]: Nsunda, K. M.; Hevesi, L. Tetrahedron Lett. 1984, 25, 4441. Comasseto, J. V.; Silveira, C. C. Synth. Commun. 1986, 16, 1167.
11. Similar reactions using others chalcogcn-stabilized carbenium ions have been described: [oxygen] Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.* Saraswathy, V. G.; Sankararaman, N. J. Chem. Soc., Perkin Trans. I 1996, 29.; [sulfur]: Paterson, I. Tetrahedron, 1988, 44, 4207.* Takeda, T.; Sugi, S.; Nakayama, A.; Suzuki, Y.; Fujiwara, T. Chem. Lett. 1992, 819. [selenium]: Nsunda, K. M.; Hevesi, L. Tetrahedron Lett. 1984, 25, 4441. Comasseto, J. V.; Silveira, C. C. Synth. Commun. 1986, 16, 1167.
12. Similar reactions using others chalcogcn-stabilized carbenium ions have been described: [oxygen] Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.* Saraswathy, V. G.; Sankararaman, N. J. Chem. Soc., Perkin Trans. I 1996, 29.; [sulfur]: Paterson, I. Tetrahedron, 1988, 44, 4207.* Takeda, T.; Sugi, S.; Nakayama, A.; Suzuki, Y.; Fujiwara, T. Chem. Lett. 1992, 819. [selenium]: Nsunda, K. M.; Hevesi, L. Tetrahedron Lett. 1984, 25, 4441. Comasseto, J. V.; Silveira, C. C. Synth. Commun. 1986, 16, 1167.
13. Similar reactions using others chalcogcn-stabilized carbenium ions have been described: [oxygen] Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.* Saraswathy, V. G.; Sankararaman, N. J. Chem. Soc., Perkin Trans. I 1996, 29.; [sulfur]: Paterson, I. Tetrahedron, 1988, 44, 4207.* Takeda, T.; Sugi, S.; Nakayama, A.; Suzuki, Y.; Fujiwara, T. Chem. Lett. 1992, 819. [selenium]: Nsunda, K. M.; Hevesi, L. Tetrahedron Lett. 1984, 25, 4441. Comasseto, J. V.; Silveira, C. C. Synth. Commun. 1986, 16, 1167.
14. Similar reactions using others chalcogcn-stabilized carbenium ions have been described: [oxygen] Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44, 4259.* Saraswathy, V. G.; Sankararaman, N. J. Chem. Soc., Perkin Trans. I 1996, 29.; [sulfur]: Paterson, I. Tetrahedron, 1988, 44, 4207.* Takeda, T.; Sugi, S.; Nakayama, A.; Suzuki, Y.; Fujiwara, T. Chem. Lett. 1992, 819. [selenium]: Nsunda, K. M.; Hevesi, L. Tetrahedron Lett. 1984, 25, 4441. Comasseto, J. V.; Silveira, C. C. Synth. Commun. 1986, 16, 1167.
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17. Mukaiyama, T. Angew. Chem. 1977, 89, 858; Angew. Chem., Int. Ed. 1977, 16, 817. Mukaiyama, T.; Murakami, M. Synthesis 1987, 1043.
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20. All compounds showed spectroscopic and analytical data consistent with the assigned structures and in accordance with the literature (cf. especially literature 7 marked with asterisk*).