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2004
Cycloaddition reactions
O 0070
Dual Behavior of Masked o-Benzoquinones in Intramolecular Diels—Alder
with Acyclic Dienes: A Rapid Entry to Polyfunctionalized Bicyc48- 032 Reactions
lo[2.2.2]oct-5-en-2-ones and cis-Decalins. — It is found that masked o-benzoquinones can act as dienes or dienophiles in Diels—Alder reactions with acyclic dienes. Their
behavior is dictated by the nature and position of the substituents in masked o-benzoquinones as well as by the structure of the acyclic dienes. In most cases the cyclization
proceeds with high regio- and stereoselectivity. Additionally, it is shown that resulting
bicyclo[2.2.2]octenone products can smoothly undergo Cope rearrangement to
cis-decalins. This offers a convenient and stereoselective approach to highly substituted
cis-decalins. — (CHEN, C.-H.; PEDDINTI, R. K.; RAO, N. S. K.; LIAO*, C.-C.;
J. Org. Chem. 69 (2004) 16, 5365-5373; Dep. Chem., Natl. Tsing Hua Univ.,
Hsinchu 30043, Taiwan; Eng.) — Jannicke
2004
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