New Dienophiles: 1‐Acetylvinyl Arenecarboxylates. Reactivity toward cyclopentadiene and exocyclic dienes
- 4 February 1981
- journal article
- research article
- Published by Wiley in Helvetica Chimica Acta
- Vol. 64 (1) , 188-197
- https://doi.org/10.1002/hlca.19810640121
Abstract
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). TheDiels‐Alderreactivity 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 dienophiles3allow direct functionalization of the position C(9) of the A‐ring of daunomycinone analogs byDiels‐Alderadditions to exocyclic dienes such as1and2.This publication has 56 references indexed in Scilit:
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