Abstract
The Stille coupling of (E)-α-stannyl-α,β-unsaturated esters with alkynyl bromides in DMF in the presence of Pd(PPh3)4 and CuI gave (Z)-2-ethoxycarbonyl-1,3-enynes in good yields. The latter underwent the palladium-catalysed hydrostannylation with tributyltin hydride in THF at room temperature to afford (1E,3E)-2-ethoxycarbonyl-3- stannyl-1,3-dienes in good yields with high regio- and stereoselectivities.
Keywords
References
1.
Naso
F.
, Pure Appl. Chem. , 1988 , 60 , 79 .
2.
Pearson
W.H.
,
Lin
K.-C.
, and
Poon
Y.-F.
, J. Org. Chem. , 1989 , 54 , 5814 .
3.
Cai
M.
,
Wang
D.
, and
Wang
P.
, J. Organomet. Chem. , 2006 , 691 , 737 .
4.
Camasseto
J.V.
, and
Brandt
C. A.
, Synthesis , 1987 , 146 .
5.
Zhu
L.S.
,
Huang
Z. Z.
, and
Huang
X.
, Tetrahedron , 1996 , 52 , 9819 .
6.
Ma
Y.
, and
Huang
X.
, J. Chem. Soc. Perkin Trans. 1 , 1997 , 2953 .
7.
Negishi
E.
, and
Luo
F. T.
, J. Org. Chem. , 1983 , 48 , 1560 .
8.
Luh
T.-Y.
, and
Wong
K.-T.
, Synthesis , 1993 , 349 .
9.
Ni
Z.-J.
,
Yang
P.-F.
,
Ng
D. K. P.
,
Tzeng
Y.-L.
, and
Luh
T.-Y.
, J. Am. Chem. Soc. , 1990 , 112 , 9356 .
10.
Suzenet
F.
,
Blart
E.
, and
Quintard
J. P.
, Synlett , 1998 , 879 .
11.
Lipshutz
B.H.
, and
Lindsley
C.
, J. Am. Chem. Soc. , 1997 , 119 , 4555 .
12.
Betzer
J.F.
,
Delaloge
F.
,
Muller
B.
, and
Pancrazi
A.
, J. Org. Chem. , 1997 , 62 , 7768 .
13.
Banert
K.
,
Fendel
W.
, and
Schlott
J.
, Angew. Chem. Int. Ed. , 1998 , 37 , 3289 .
14.
Wang
C.
,
Song
Q.
, and
Xi
Z.
, Tetrahedron , 2004 , 60 , 5207 .
15.
Li
J.-H.
,
Liang
Y.
, and
Xie
Y.-X.
, J. Org. Chem. , 2004 , 69 , 8125 .
16.
Herndon
J.W.
, and
Patel
P. P.
, J. Org. Chem. , 1996 , 61 , 4500 .
17.
Desurmont
G.
,
Dalton
S.
,
Giolando
D. M.
, and
Srebnik
M.
, J. Org. Chem. , 1996 , 61 , 7943 .
18.
Zhao
H.
,
Yang
W.
,
Xie
S.
, and
Cai
M.
, Eur. J. Org. Chem. , 2012 , 831 .
19.
Trost
B.M.
,
Vladuchick
W. C.
, and
Bridges
A. J.
, J. Am. Chem. Soc. , 1980 , 102 , 3554 .
20.
Padwa
A.
, and
Norman
B. H.
, Tetrahedron Lett. , 1988 , 29 , 2417 .
21.
Pegram
J.J.
, and
Anderson
C. B.
, Tetrahedron Lett. , 1988 , 29 , 6719 .
22.
Aversa
M.C.
,
Barattucci
A.
,
Bonaccorsi
P.
,
Giannetto
P.
, and
Jones
D. N.
, J. Org. Chem. , 1997 , 62 , 4376 .
23.
Su
M.
,
Kang
Y.
,
Yu
W.
,
Hua
Z.
, and
Jin
Z.
, Org. Lett. , 2002 , 4 , 691 .
24.
Coleman
R.S.
, and
Walczak
M. C.
, Org. Lett. , 2005 , 7 , 2289 .
25.
Cai
M.-Z.
,
Zhou
Z.
, and
Wang
P.-P.
, Synthesis , 2006 , 789 .
26.
Rossi
R.
,
Carpita
A.
, and
Cossi
P.
, Tetrahedron Lett. , 1992 , 33 , 4495 .
27.
Smith
N.D.
,
Mancuso
J.
, and
Lautens
M.
, Chem. Rev. , 2000 , 100 , 3257 .
28.
Trost
B.M.
, and
Li
C.-J.
, Synthesis , 1994 , 1267 .
29.
Alami
M.
, and
Ferri
F.
, Synlett , 1996 , 755 .
30.
Ferri
F.
, and
Alami
M.
, Tetrahedron Lett. , 1996 , 37 , 7971 .
31.
Leusink
A.J.
,
Budding
H. A.
, and
Marsman
J. W.
, J. Organomet. Chem. , 1967 , 9 , 285 .