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Volumn 125, Issue 32, 2003, Pages 9682-9688

Indium-mediated β-allylation, β-propargylation, and β-allenylation onto α,β-unsaturated ketones: Reactions of in-situ-generated 3-tert-butyldimethylsilyloxyalk-2-enylsulfonium salts with in-situ-generated organoindium reagents

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SALTS; SUBSTITUTION REACTIONS;

EID: 0042125246     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035988m     Document Type: Article
Times cited : (40)

References (91)
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    • For a preliminary letter of this work, see: (a) Lee, P. H.; Lee, K.; Kim, S. Org. Lett. 2001, 3, 3205. (b) Iwasawa, N.; Miura, T.; Kiyota, K.; Kusama, H.; Lee, K.; Lee, P. H. Org. Lett. 2002, 4, 4463. (c) Miura, T.; Kiyota, K.; Kusama, H.; Lee, K.; Kim, H.; Kim, S.; Lee, P. H.; Iwasawa, N. Org. Lett. 2003, 5, 1725.
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    • Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions are reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuds, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
    • (2002) Angew. Chem., Int. Ed. , vol.41 , pp. 1389
    • Shibata, I.1    Kano, T.2    Kanazawa, N.3    Fukuoka, S.4    Baba, A.5
  • 77
    • 0000862956 scopus 로고
    • Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions are reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuds, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
    • (1990) J. Org. Chem. , vol.55 , pp. 4853
    • Haruta, J.1    Nishi, K.2    Matsuds, S.3    Akai, S.4    Tamura, Y.5    Kita, Y.6
  • 78
    • 0000997935 scopus 로고
    • Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions are reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuds, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 719
    • Corey, E.J.1    Rucker, C.2
  • 79
    • 0000434822 scopus 로고
    • Generally, 1,4-propargylation onto α,β-unsaturated ketones is not an easy process because 1,2-addition of propargyl (or allenyl) metallic reagents usually occurs preferentially. Some exceptions are reported using allenyltin and several other reagents; see: (a) Shibata, I.; Kano, T.; Kanazawa, N.; Fukuoka, S.; Baba, A. Angew. Chem., Int. Ed. 2002, 41, 1389. (b) Haruta, J.; Nishi, K.; Matsuds, S.; Akai, S.; Tamura, Y.; Kita, Y. J. Org. Chem. 1990, 55, 4853. (c) Corey, E. J.; Rucker, C. Tetrahedron Lett. 1982, 23, 719. (d) Paquette, L. A.; Han, Y.-K. J. Am. Chem. Soc. 1981, 103, 1831.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 1831
    • Paquette, L.A.1    Han, Y.-K.2
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    • note
    • 5 and a silyl chloride such as TMSCl or TBSCl, only hydrolyzed conjugate adduct was obtained, and none of the desired silyl enol ether was detected in the crude mixtures.


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