Abstract
(E)-α-Stannyl-α,β-unsaturated esters underwent an iododestannylation reaction to afford (E)-α-iodo-α,β-unsaturated esters, which reacted with (E)-alkenylzirconium(IV) complexes produced in situ by hydrozirconation of terminal alkynes in the presence of Pd(PPh3)4 to afford stereoselectively a variety of 1,3-dien-2-yl esters in good yields.
Keywords
References
1.
Mori K.
, The total synthesis of natural products: the synthesis of insect pheromones ,
ApSimon J.
ed., Vol. 4 , Wiley , New York , 1981 .
2.
Zeng X.
,
Qian M.
,
Hu Q.
, and
Negishi E.-I.
, Angew. Chem. Int. Ed. , 2004 , 43 , 2259 .
3.
Arce E.
,
Carreno M. C.
,
Cid M. B.
, and
Ruano J. L. G.
, J. Org. Chem. , 1994 , 59 , 3421 .
4.
Ghosal S.
,
Luke S. P.
, and
Tyler K. S.
, J. Org. Chem. , 1987 , 52 , 4296 .
5.
Negishi E.
,
Takahashi T.
,
Baba S.
,
Van Horn D. E.
, and
Okukado N.
, J. Am. Chem. Soc. , 1987 , 109 , 2393 .
6.
Chan K.S.
, and
Mak C. C.
, Tetrahedron , 1994 , 50 , 2003 .
7.
Kasatkin A.
, and
Whitby R. J.
, J. Am. Chem. Soc. , 1999 , 121 , 7039 .
8.
Molander G.A.
, and
Yokoyama Y.
, J. Org. Chem. , 2006 , 71 , 2493 .
9.
Deagostino A.
,
Prandi C.
,
Zavattaro C.
, and
Venturello P.
, Eur. J. Org. Chem. , 2006 , 2463 .
10.
Padwa A.
,
Harrison B.
,
Murphree S. S.
, and
Yeske P. E.
, J. Org. Chem. , 1989 , 54 , 4232 .
11.
Yoshimatsu M.
, and
Hasegawa J.
, J. Chem. Soc., Perkin Trans. 1 , 1997 , 211 .
12.
Negishi E.
, and
Luo F. T.
, J. Org. Chem. , 1983 , 48 , 1560 .
13.
Ni Z.J.
,
Yang P. F.
,
Ng D. K. P.
,
Tzeng Y. L.
, and
Luh T. Y.
, J. Am. Chem. Soc. , 1990 , 112 , 9356 .
14.
Cai M.
,
Hao W.
,
Zhao H.
, and
Song C.
, J. Organomet. Chem. , 2003 , 679 , 14 .
15.
Pearson W.H.
,
Lin K.-C.
, and
Poon Y.-F.
, J. Org. Chem. , 1989 , 54 , 5814 .
16.
Grieco P.A.
,
May S. A.
, and
Kaufman M. D.
, Tetrahedron Lett. , 1998 , 39 , 7047 .
17.
Cai M.
,
Wang D.
, and
Wang P.
, J. Organomet. Chem. , 2006 , 691 , 737 .
18.
Hevesi L.
,
Hermans B.
, and
Allard C.
, Tetrahedron Lett. , 1994 , 35 , 6729 .
19.
Ma Y.
, and
Huang X.
, J. Chem. Soc., Perkin Trans. 1 , 1997 , 2953 .
20.
Cai M.
,
Huang J.
, and
Peng C.
, J. Organomet. Chem. , 2003 , 681 , 98 .
21.
Xie M.H.
, and
Huang X.
, Chin. J. Chem. , 2004 , 22 , 184 .
22.
Cai M.
,
Chen G.
, and
Hao W.
, Synthesis , 2007 , 1197 .
23.
Suzenet F.
,
Blart E.
, and
Quintard J. P.
, Synlett , 1998 , 879 .
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.
Hoffmann H.M. R.
, and
Rabe J.
, Angew. Chem. Int. Ed. Engl. , 1983 , 22 , 795 .
27.
Hudlicky T.
,
Short R. P.
,
Ranu B. C.
, and
Revol J. M.
, J. Org. Chem. , 1983 , 48 , 4453 .
28.
Kende A.S.
, and
Toder B. H.
, J. Org. Chem. , 1982 , 47 , 163 .
29.
Corey E.J.
, and
Erickson B. W.
, J. Org. Chem. , 1974 , 39 , 821 .
30.
Pornet J.
,
Rayadh A.
, and
Miginiac L.
, Tetrahedron Lett. , 1988 , 29 , 3065 .
31.
Tsuda T.
,
Yoshida T.
, and
Saegusa T.
, J. Org. Chem. , 1988 , 53 , 607 .
32.
Janecki T.
, and
Bodalski R.
, Synthesis , 1989 , 506 .
33.
Palmelund A.
,
Myers E. L.
,
Tai L. R.
,
Tisserand S.
,
Butts C. P.
, and
Aggarwal V. K.
, Chem. Commun. , 2007 , 4128 .
34.
Rossi R.
,
Carpita A.
, and
Cossi P.
, Tetrahedron Lett. , 1992 , 33 , 4495 .
35.
Negishi E.
,
Okukado H.
,
King A. O.
,
Van Horn D. E.
, and
Spiegel B. I.
, J. Am. Chem. Soc. , 1978 , 100 , 2254 .