Note
Novel Stereoselective Synthesis of (E)-β-Silylvinylstannanes via Hydromagnesiation of Silylarylacetylenes
Bin Huang,
Zhou Zhou,
Ming-Zhong Cai,
Bin Huang
Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorZhou Zhou
Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorBin Huang,
Zhou Zhou,
Ming-Zhong Cai,
Bin Huang
Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorZhou Zhou
Department of Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330027, China
Search for more papers by this authorAbstract
Hydromagnesiation of silylarylacetylenes 1 in diethyl ether gave (E)-β-silylvinyl Grignard reagents 2, which reacted with trialkylstannyl chlorides 3 to afford stereoselectively (E)-β-silylvinylstannanes 4 in good yields.
REFERENCES
- 1 Marfat, P. R.; McGuirk, P.; Helquist, P.. J. Org. Chem., 1979, 44, 3888.
- 2 Obayashi, M.; Utimoto, K.; Nozaki, H.. Bull. Chem. Soc. Jpn., 1979, 52, 1760.
- 3 Masaki, Y.; Sakuma, K.; Kaji, K.. J. Chem. Soc., Chem. Commun., 1980, 434.
- 4 Magrietis, P. A.; Scott, M. E.; Kim, K. D.. Tetrahedron Lett., 1991, 32, 6085.
- 5 Sharma, S.; Oehlschlager, A. C.. Tetrahedron Lett., 1986, 27, 6161.
- 6 Hibino, J. C.; Matsubara, S.; Morizawa, Y.. Tetrahedron Lett., 1984, 25, 2151.
- 7a Lipschutz, B. H.; Bhandari, A.; Lindsley, C.; Keil, R.; Wood, M. R.. Pure Appl. Chem., 1994, 66, 1493.
- 7b Lipschutz, B. H.; Keil, R.; Barton, J. C.. Tetrahedron Lett., 1992, 33, 5861.
- 7c Dabdoub, M. J.; Baroni, A. C. M.. J. Org. Chem., 2000, 65, 54.
- 8a
Huang, X.;
Ma, Y..
Synthesis,
1997,
417.
10.1055/s-1997-1203 Google Scholar
- 8b Ma, Y.; Li, B.; Huang, X.. J. Organomet. Chem., 1999, 590, 234.
- 9 Sato, F.. J. Organomet. Chem., 1985, 285, 53.
- 10a Sun, A.; Huang, X.. Synthesis, 2000, 775.
- 10b Arefolov, A.; Langille, N. F.; Panek, J. S.. Org. Lett., 2001, 3, 3281.
- 11a
Smith, P. J., Chemistry of Tin, Blackie, New York, 1998.
10.1007/978-94-011-4938-9 Google Scholar
- 11b Farina, V.; Krishnamurthy, V.; Scott, W.. Org. React., 1997, 50, 1.
- 12a Chan, T. H.; Fleming, I.. Synthesis, 1979, 761.
- 12b Colvin, E. W., Silicon Reagents in Organic Synthesis, Academic, London, 1988.
- 13 Mitchell, T. N.; Wickenkamp, R.; Amamria, A.; Schneider, U.. J. Org. Chem., 1987, 52, 4868.
- 14 Cuadrado, P.; Gonzalez-Nogal, A. M.; Sanchez, A.. J. Org. Chem., 2001, 66, 1961.
- 15 Sato, F.; Watanabe, H.; Tanaka, Y.; Yamaji, T.; Sato, M.. Tetrahedron Lett., 1983, 24, 1041.
- 16 Alami, M.; Ferri, F.; Linstrumelle, G.. Tetrahedron Lett., 1993, 34, 6403.
- 17a Grobel, B. T.; Seebach, D.. Chem. Ber., 1977, 110, 867.
- 17b Pelter, A.; Smith, K.; Parry, D. E.; Jones, K. D.. Aust. J. Chem., 1992, 45, 57.
- 18a Miller, R. B.; McGarvey, G.. J. Org. Chem., 1978, 43, 4424.
- 18b Hudrlik, P. F.; Agwaramgbo, E. L. O.; Hudrlik, A. M.. J. Org. Chem., 1989, 54, 5613.
