TY - JOUR
T1 - Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues
AU - Terakado, Masahiko
AU - Murai, Kouya
AU - Miyazawa, Masahiro
AU - Yamamoto, Keiji
N1 - Funding Information:
Supportb y a Grant-in-Aid for General Scientific Research( No. 04403018)f rom the Ministry of Education,S cience,a nd Culture,J apan is gratefullya cknowledgedW. e are indebtedt o Mr. K. Takatsuna (TonenC o.Ltd.)f or HRMS measuremenotf 2b.
PY - 1994
Y1 - 1994
N2 - The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via π-allylpalladium species were preceded by their intramolecular olefin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.
AB - The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via π-allylpalladium species were preceded by their intramolecular olefin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.
UR - http://www.scopus.com/inward/record.url?scp=0028337115&partnerID=8YFLogxK
U2 - 10.1016/S0040-4020(01)85639-8
DO - 10.1016/S0040-4020(01)85639-8
M3 - 学術論文
AN - SCOPUS:0028337115
SN - 0040-4020
VL - 50
SP - 5705
EP - 5718
JO - Tetrahedron
JF - Tetrahedron
IS - 19
ER -