TY - JOUR
T1 - New Dienophiles
T2 - 1‐Acetylvinyl Arenecarboxylates. Reactivity toward cyclopentadiene and exocyclic dienes
AU - Tamariz, Joaquin
AU - Vogel, Pierre
PY - 1981/2/4
Y1 - 1981/2/4
N2 - The preparations of 1‐acetylvinyl arenecarboxylates H2C=C(COCH3)OCOR with R = phenyl, p‐nitrophenyl, 2,4‐dinitrophenyl, α‐ and β‐naphthyl are described 3. The Diels‐Alder reactivity of these dienophiles toward cyclopentadiene is evaluated and compared with that of methyl vinylketone, 3‐trimethylsilyloxy‐, 3‐ethoxy‐ and 3‐acetoxy‐3‐buten‐2‐ones. The stereoselectivity of the cycloadditions of these dienophiles with 2,3,5,6‐tetramethylidene‐7‐oxanorbornane 1 and 5,8‐dimethoxy‐1,4‐epoxy‐2,3‐dimethylidene‐1,2,3,4‐tetrahydroanthracene 2 is studied. In principle, the dienophiles 3 allow direct functionalization of the position C(9) of the A‐ring of daunomycinone analogs by Diels‐Alder additions to exocyclic dienes such as 1 and 2.
AB - The preparations of 1‐acetylvinyl arenecarboxylates H2C=C(COCH3)OCOR with R = phenyl, p‐nitrophenyl, 2,4‐dinitrophenyl, α‐ and β‐naphthyl are described 3. The Diels‐Alder reactivity of these dienophiles toward cyclopentadiene is evaluated and compared with that of methyl vinylketone, 3‐trimethylsilyloxy‐, 3‐ethoxy‐ and 3‐acetoxy‐3‐buten‐2‐ones. The stereoselectivity of the cycloadditions of these dienophiles with 2,3,5,6‐tetramethylidene‐7‐oxanorbornane 1 and 5,8‐dimethoxy‐1,4‐epoxy‐2,3‐dimethylidene‐1,2,3,4‐tetrahydroanthracene 2 is studied. In principle, the dienophiles 3 allow direct functionalization of the position C(9) of the A‐ring of daunomycinone analogs by Diels‐Alder additions to exocyclic dienes such as 1 and 2.
UR - http://www.scopus.com/inward/record.url?scp=84985138659&partnerID=8YFLogxK
U2 - 10.1002/hlca.19810640121
DO - 10.1002/hlca.19810640121
M3 - Artículo
AN - SCOPUS:84985138659
SN - 0018-019X
VL - 64
SP - 188
EP - 197
JO - Helvetica Chimica Acta
JF - Helvetica Chimica Acta
IS - 1
ER -