TY - JOUR
T1 - Regioselective Multicomponent Synthesis of 2,4,6-Trisubstituted Phenols from Fischer Alkynyl Carbene Complexes
AU - López, Julio
AU - De La Cruz, Fabiola N.
AU - Flores-Conde, María Inés
AU - Flores-Álamo, Marcos
AU - Delgado, Francisco
AU - Tamariz, Joaquín
AU - Vázquez, Miguel A.
N1 - Publisher Copyright:
Copyright © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
PY - 2016/3/1
Y1 - 2016/3/1
N2 - A series of 2,4,6-trisubstituted phenols 7a-7p has been prepared in moderate to good yields (23-77 %) by a retro-Diels-Alder reaction from hindered tricyclic alcohols 6a-6q, using mild acidic conditions. The tricyclic alcohols were obtained by reduction of highly functionalized cyclohexadienones 5a-5q, which in turn were regioselectively prepared under mild conditions in high yields by treatment of a series of stable chromium(0) and tungsten(0) Fischer dienyl carbenes 4a-4g with different terminal alkynes 3a-3l. Carbenes 4a-4g were prepared by a [4+2] cycloaddition of alkynylethoxy carbene complexes 1a-1g with 1,2,3,4,5-pentamethylcyclopentadiene (2). In a complementary route, compounds 5a-5q were also obtained by a multicomponent reaction in yields similar to those obtained in the multistep process (25-84 %), starting from 1a-1g, 2, and 3a-3l. The phenol products have a wide range of potential applications, and may be useful intermediates for further transformations. 2,4,6-Trisubstituted phenols were prepared by a retro-Diels-Alder reaction from hindered tricyclic alcohols under acidic conditions. The tricyclic alcohols were obtained by the reduction of cyclohexadienones, which in turn were prepared by the reaction of Fischer dienyl carbenes with terminal alkynes. The dienyl carbenes were prepared from alkynyl Fischer carbenes and pentamethylcyclopentadiene.
AB - A series of 2,4,6-trisubstituted phenols 7a-7p has been prepared in moderate to good yields (23-77 %) by a retro-Diels-Alder reaction from hindered tricyclic alcohols 6a-6q, using mild acidic conditions. The tricyclic alcohols were obtained by reduction of highly functionalized cyclohexadienones 5a-5q, which in turn were regioselectively prepared under mild conditions in high yields by treatment of a series of stable chromium(0) and tungsten(0) Fischer dienyl carbenes 4a-4g with different terminal alkynes 3a-3l. Carbenes 4a-4g were prepared by a [4+2] cycloaddition of alkynylethoxy carbene complexes 1a-1g with 1,2,3,4,5-pentamethylcyclopentadiene (2). In a complementary route, compounds 5a-5q were also obtained by a multicomponent reaction in yields similar to those obtained in the multistep process (25-84 %), starting from 1a-1g, 2, and 3a-3l. The phenol products have a wide range of potential applications, and may be useful intermediates for further transformations. 2,4,6-Trisubstituted phenols were prepared by a retro-Diels-Alder reaction from hindered tricyclic alcohols under acidic conditions. The tricyclic alcohols were obtained by the reduction of cyclohexadienones, which in turn were prepared by the reaction of Fischer dienyl carbenes with terminal alkynes. The dienyl carbenes were prepared from alkynyl Fischer carbenes and pentamethylcyclopentadiene.
KW - Alkynes
KW - Carbene ligands
KW - Cycloaddition
KW - Fischer carbenes
KW - Phenols
UR - http://www.scopus.com/inward/record.url?scp=84959895832&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201501211
DO - 10.1002/ejoc.201501211
M3 - Artículo
SN - 1434-193X
VL - 2016
SP - 1314
EP - 1323
JO - European Journal of Organic Chemistry
JF - European Journal of Organic Chemistry
IS - 7
ER -