Abstract
(E)-3-alkenyl acetates, which are insect sex pheromone constituents, have been prepared from linear saturated aldehydes, by a short three steps process, via the (E)-3-alkenoic acids and the corresponding (E)-3-alkenols, in good overall yield (60–65%) and high stereochemical purity (>99%).
Keywords
References
1.
Renou M.
,
Descoins Ch.
,
Lallemand J.Y.
,
Priesner E.
,
Lettere M.
and
Gallois M.
, Z. Angew. Entomol. , 1980 , 90 , 275 .
2.
Baker R.
,
Herbert R.H.
,
Neequaye N.N.
and
Rao K.N.
, J. Chem. Ecol. , 1985 , 11 , 989 .
3.
Griepink F.C.
,
van Beek T.A.
,
Hans Visser J.
,
Voerman S.
and
De Groot A.
, J. Chem. Ecol. , 1995 , 12 , 2003 .
4.
(a)
Toth M.
and
Doolittle R.E.
, J. Chem. Ecol . 1992 , 18 , 1093 ;
5.
Toth M.
and
Doolittle R.E.
, Entomol. Exp. Appl. , 1995 , 77 , 347 .
6.
Cheskis B.A.
,
Ivanova N.M.
,
Moiseenkov A.M.
and
Nefedof O.M.
, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) , 1990 , 39 , 1839 .
7.
Ivanova N.M.
,
Cheskis B.A.
,
Rubanova E.V.
,
Yatsynin V.G.
,
Moiseenkov A.M.
and
Nefedov O.M.
, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) , 1991 , 40 , 557 .
8.
Ragoussis N.
and
Ragoussis V.
, J. Chem. Soc., Perkin Trans. 1 , 1998 , 3529 .
9.
Bazant V.
,
Capka M.
,
Cerny M.
,
Chvalovsky V.
,
Kochloefl K.
,
Kraus M.
and
Malek J.
, Tetrahedron Lett. 1968 , 29 , 3303 .
10.
Soai K.
,
Yokoyama S.
and
Mochida K.
, Synthesis , 1987 , 647 .
11.
Berkenbusch T.
and
Bruckner R.
, Tetrahedron , 1998 , 54 , 11471 .
12.
Patterson J.W.
, Synthesis , 1985 , 337 .
13.
Mori K.
and
Kinsho T.
, Liebigs Ann. Chem. , 1988 , 807 .
