Abstract
Hydromagnesiation of alkylarylacetylenes 1 in diethyl ether gave (E)-α-arylvinyl Grignards reagents 2, which reacted with arylsulfenyl chlorides 3 to afford stereoselectively (E)-1,2-disubstituted vinyl sulfides 4 in good yields.
Keywords
References
1.
(a)
Trost B.M.
, and
Lavoie A. C.
, J. Am. Chem. Soc. , 1983 , 105 , 5075 .
2.
Fiandanese V.
,
Marchese G.
,
Naso F.
, and
Ronzini L.
, J. Chem. Soc., Chem. Commun. , 1982 , 647 .
3.
Luh T.-Y.
, and
Ni Z.-J.
, Synthesis , 1990 , 89 .
4.
Babudri F.
,
Fiandanese V.
,
Mazzone L.
, and
Naso F.
, Tetrahedron Lett. , 1994 . 35 , 8847 .
5.
(a)
Kakimoto M.
,
Yamamoto T.
, and
Okawara M.
, Tetrahedron Lett. , 1979 , 623 .
6.
Cohen T.
,
Herman G.
,
Falck J. R.
, and
Mura A. J.
, J. Org. Chem. , 1975 , 40 , 812 .
7.
Brown H.C.
, and
Rei M. H.
, J. Am. Chem. Soc. , 1969 , 91 , 5646 .
8.
Alexakis A.
,
Cahiez G.
,
Normant J. F.
, and
Villieras J.
, Bull. Soc. Chim. Fr. , 1977 , 693 .
9.
(a)
Wakefield B.J.
, in: Comprehensive Organometallic Chemistry , Vol. 7 ,
Wilkinson G.
, Ed., Pergamon Press , Oxford , 1982 , p. 1 .
10.
Alexakis A.
, and
Normant J. F.
, Synthesis , 1985 , 72 .
11.
Sato F.
,
Ishikawa H.
, and
Sato M.
, Tetrahedron Lett. , 1981 , 22 , 85 .
12.
Sato F.
,
Watanabe H.
,
Tanaka Y.
,
Yamaji T.
, and
Sato M.
, Tetrahedron Lett. , 1983 , 24 , 1041 .
13.
Cai M.
,
Peng C.
,
Zhao H.
, and
Hao W.
, J. Chem. Res. , 2003 , 296 .
14.
Zhao H.
, and
Cai M.
, Synthesis , 2002 , 1347 .
15.
Cai M.
,
Hao W.
,
Zhao H.
, and
Song C.
, J. Organomet. Chem. , 2003 , 679 , 14 .
16.
Cai M.
,
Hao W.
,
Zhao H.
, and
Xia J.
, J. Organomet. Chem. , 2004 , 689 , 1714 .
17.
Alami M.
,
Ferri F.
, and
Linstrumelle G.
, Tetrahedron Lett. , 1993 , 34 , 6403 .
18.
Harpp D.N.
,
Friedlander B. T.
, and
Smith R. A.
, Synthesis , 1979 , 181 .
