Abstract
Hydrozirconation of terminal alkynes 1 gives (E)-alkenylzirconium complexes 3, which when cross-coupled with α-iodoethenylstannanes 4 in the presence of [Pd(PPh3)4] catalyst afford stereoselectively (3E)-2-stannyl-1,3-dienes 5 in good yields.
References
1.
(a)
Mori K.
, The synthesis of insect pheromones , In The Total Synthesis of Natural Products ,
ApSimon J.
(ed.) Vol. 4 , Wiley , New York , 1981 .
2.
Huang Y.Z.
,
Shi L.
,
Yang J.
, and
Zhang J.
, Tetrahedron Lett. , 1987 , 28 , 2159 .
3.
Naso F.
, Pure Appl. Chem. , 1988 , 60 , 79 .
4.
Fiandanese V.
, Pure Appl. Chem. , 1990 , 62 , 1987 .
5.
(a)
Oppolzer W.
, Angew. Chem., Int. Ed. Engl. , 1984 , 23 , 876 .
6.
Arce E.
,
Carreno M. C.
,
Cid M. B.
, and
Ruano J. L. G.
, J. Org. Chem. , 1994 , 59 , 3421 .
7.
Ghosal S.
,
Luke S. P.
, and
Tyler K. S.
, J. Org. Chem. , 1987 , 52 , 4296 .
8.
(a)
Ideses R.
, and
Shani A.
, Tetrahedron , 1989 , 45 , 3523 .
9.
Baudin J.B.
,
Hareau G.
,
Julia S. A.
,
Lorne R.
, and
Ruel O.
, Bull. Soc. Chem. Fr. , 1993 , 130 , 856 .
10.
(a)
Negishi E.
,
Takahashi T.
,
Baba S.
,
Van Horn D. E.
, and
Okukado N.
, J. Am. Chem. Soc. , 1987 , 109 , 2393 .
11.
Stille J.K.
, and
Groh B. L.
, J. Am. Chem. Soc. , 1987 , 109 , 813 .
12.
Chan K.S.
, and
Mark C. C.
, Tetrahedron , 1994 , 50 , 2003 .
13.
(a)
Chan T.H.
, and
Li J. S.
, J. Chem. Soc., Chem. Commun. , 1982 , 696 .
14.
Luh T.Y.
, and
Wong K. T.
, Synthesis , 1993 , 349 .
15.
Babudri F.
,
Fiandanese V.
,
Mazzone L.
, and
Naso F.
, Tetrahedron Lett. , 1994 , 35 , 8847 .
16.
(a)
Comasseto J.V.
, and
Brandt C. A.
, Synthesis , 1987 , 146 .
17.
Zhu L.S.
,
Huang Z. Z.
, and
Huang X.
, Tetrahedron , 1996 , 52 , 9819 .
18.
Ma Y.
, and
Huang X.
, J. Chem. Soc., Perkin Trans. 1 , 1997 , 2953 .
19.
(a)
Gschneidner D.
, J. Am. Chem. Soc. , 1993 , 115 , 6625 .
20.
Stille J.K.
, Angew. Chem. Int. Ed. Engl. , 1986 , 25 , 508 .
21.
(a)
Betzer J.F.
, and
Pancrazi A.
, Synlett , 1998 , 1129 .
22.
Suzenet F.
,
Blart E.
, and
Quintard J. P.
, Synlett , 1998 , 879 .
23.
Piers E.
, and
Morton H. E.
, J. Org. Chem. , 1980 , 45 , 4263 .
24.
Lipshutz B.H.
, and
Lindsley C.
, J. Am. Chem. Soc. , 1997 , 119 , 4555 .
25.
Betzer J.F.
,
Delaloge F.
,
Muller B.
, and
Pancrazi A.
, J. Org. Chem. , 1997 , 62 , 7768 .
26.
(a)
Negishi E.
,
Okukado H.
,
King A. O.
,
Van Horn D. E.
, and
Spiegel B. I.
, J. Am. Chem. Soc. , 1978 , 100 , 2254 .
27.
Negishi E.
, and
Van Horn D. E.
, J. Am. Chem. Soc. , 1977 , 99 , 3168 .
28.
(a)
Lipshuts B.H.
,
Keil R.
, and
Barton J. C.
, Tetrahedron Lett. , 1992 , 33 , 5861 .
29.
Cai M.
,
Zhao H.
,
Ye H.
,
Xia J.
, and
Song C.
, J. Chem. Res.(S) , 2003 , 344 .
30.
Buchwald S.L.
,
LaMaire S. J.
,
Nielsen R. B.
,
Watson B. T.
, and
King S. M.
, Tetrahedron Lett. , 1987 , 28 , 3895 .
