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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.
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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.
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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.
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Paquette, L.A.1
Han, Y.-K.2
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80
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0041641790
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note
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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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82
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0042142761
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Speziale, A. J.; Tung, C. C.; Ratts, K. W.; Yao, A. J. Am. Chem. Soc. 1965, 87, 962.
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Speziale, A.J.1
Tung, C.C.2
Ratts, K.W.3
Yao, A.4
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18544384775
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Franzen, V.; Schmidt, H. J.; Mertz, C. Chem. Ber. 1961, 94, 2942.
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Franzen, V.1
Schmidt, H.J.2
Mertz, C.3
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(c) Matsuyama, H.; Nakamura, T.; Kamigata, N. J. Org. Chem. 1989, 54, 5218.
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Matsuyama, H.1
Nakamura, T.2
Kamigata, N.3
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