Abstract
A combination of the Homer–Emmons synthesis of alkyl 2,4-dienoates with their hydrogenation over complex L·Cr(CO)3 catalysts (L = arene or 3CO) provides a versatile, stereocontrolled approach to olefins with a homoallylic pattern of functional substitution, such as certain insect pheromones or (Z)-prenylated arenes analogous to the “left-side” moiety of bifurcarenone.
References
1.
Maryanoff B.E., Reitz A.B.
Chemical Reviews,
1989
2.
10.1070/MC1995v005n02ABEH000448_bib1_2
Kryshtal
Izv. Akad. Nauk, Ser. Khim.,
1993
3.
Sodeoka M., Shibasaki M.
Synthesis,
1993
4.
Vasil’ev A.A., Serebryakov E.P.
Mendeleev Communications,
1994
5.
Naruse Y., Toru E., Hisashi Y.
Tetrahedron Letters,
1988
6.
Sodeoka M., Shibasaki M.
Journal of Organic Chemistry,
1985
7.
SODEOKA M., IIMORI T., SHIBASAKI M.
Chemical and Pharmaceutical Bulletin,
2011
8.
Johnston B.D., Oehlschlager A.C.
Journal of Organic Chemistry,
1986
9.
10.
Naoshima Y., Munakata Y., Funai A.
Bioscience, Biotechnology and Biochemistry,
1992
11.
10.1070/MC1995v005n02ABEH000448_bib8_1
Tai
Chem. Pharm. Bull.,
1971
12.
Howard R., Matsumura F., Coppel H.C.
Journal of Chemical Ecology,
1976
13.
Sun H.H., Ferrara N.M., McConnell O.J., Fenical W.
Tetrahedron Letters,
1980
14.
Francisco C., Banaigs B., Teste J., Cave A.
Journal of Organic Chemistry,
1986
15.
Cork A., Hall D.R., Blaney W.M., Simmonds M.S.
Tetrahedron Letters,
1991
16.
10.1070/MC1995v005n02ABEH000448_bib11
Mavrov
Izv. Akad. Nauk, Ser. Khim.,
1993
17.
Fukui H., Matsumura F., Ma M.C., Burkholder W.E.
Tetrahedron Letters,
1974
18.
Ma M., Hummel H.E., Burkholder W.E.
Journal of Chemical Ecology,
1980