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New Dienophiles: 1‐Acetylvinyl Arenecarboxylates. Reactivity toward cyclopentadiene and exocyclic dienes
Author(s) -
Tamariz Joaquin,
Vogel Pierre
Publication year - 1981
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19810640121
Subject(s) - chemistry , cyclopentadiene , reactivity (psychology) , stereoselectivity , ring (chemistry) , regioselectivity , stereochemistry , cycloaddition , diels–alder reaction , bicyclic molecule , medicinal chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
The preparations of 1‐acetylvinyl arenecarboxylates H 2 C=C(COCH 3 )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 .