Hydromagnesiation of alkylarylacetylenes 1 in diethyl ether gave (E)-α-arylvinyl Grignard reagents 2, which reacted with aldehydes or ketones 3 to afford stereoselectively (E)-2,3-disubstituted allylic alcohols 4 in good yields.
JonesT.K., and DenmarkS. E., Org. Synth., 1990, Coll. Vol.7, 524; D.J. Faulkner, Synthesis, 1971, 175; J. Reucroft and P.G. Sammes, Q. Rev. Chem. Soc., 1971, 25, 135; R.M. Magid, O.S. Fruchey, W.L. Johnson and T.G. Allen, J. Org. Chem., 1979, 44, 359; K. Takai, S. Sakamoto and T. Isshiki, Org. Lett., 2003, 5, 653; S. Okamoto, H. Tsujiyama, T. Yoshino and F. Sato, Tetrahedron Lett., 1991, 32, 5789; Y.K. Chen and P.J. Walsh, J. Am. Chem. Soc., 2004, 126, 3702.
2.
DuboudinJ.G., and JousseaumeB., J. Organomet. Chem., 1979, 168, 1; M. Zaidlewicz, A. Uzarewicz and R. Sarnowski, Synthesis, 1979, 62; A. Ogawa, Y. Tsuboi, R. Obayashi, K. Yokoyama, I. Ryu and N. Sonoda, J. Org. Chem., 1994, 59, 1600; E. Negishi, Y. Zhang, F. E. Cederbaum and M.B. Webb, J. Org. Chem., 1986, 51, 4080; K. Takai, Y. Kataoka and K. Utimoto, J. Org. Chem., 1990, 55, 1707; A. Kamimura and N. Ono, J. Chem. Soc., Chem. Commun., 1988, 1278; M. Yukio, S. Kazuhiko and K. Kenji, Chem. Pharm. Bull., 1985, 33, 2531; M. Julia and J.N. Verpeaux, Tetrahedron, 1983, 39, 3289.
3.
OppolzerW., and RadinovR. N., Helv. Chim. Acta, 1992, 75, 170.
4.
MillerK.M., HuangW. S., and JamisonT. F., J. Am. Chem. Soc., 2003, 125, 3442.
5.
ChanJ., and JamisonT. F., J. Am. Chem. Soc., 2003, 125, 11514.
6.
WipfP., and RibeS., J. Org. Chem., 1998, 63, 6454.
7.
ChenY.K., LurainA. E., and WalsonP. J., J. Am. Chem. Soc., 2002, 124, 12225.
8.
KangY.H., LeeC. J., and KimK., J. Org. Chem., 2001, 66, 2149.
9.
SatoF., IshikawaH., and SatoM., Tetrahedron Lett., 1981, 22, 85.
