Cross-Coupling for Cross-Conjugation: Practical Synthesis and Diels−Alder Reactions of [3]Dendralenes
- 11 October 2007
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (23) , 4861-4864
Abstract
The parent [3]dendralene and 2-substituted [3]dendralenes are made easily through cross-coupling reactions. Contrary to some earlier reports, [3]dendralene is sufficiently stable to be handled using standard synthetic methods. These compounds allow the one-step stereoselective construction of polycyclic frameworks through reactions with dienophiles. Site selectivity and stereoselectivity in Diels−Alder reactions with dienophiles are generally not influenced by the nature of the [3]dendralene's 2-substituent; these features can, however, be influenced with Lewis acids.Keywords
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