Abstract
The palladium-catalyzed tandem cyclization-coupling reaction of conjugated enynes having a stabilizing carbon nucleophile with aryl iodides and vinyl halides or triflates produced stereodefined, functionalized five- and six-membered 1,3-bis-exocyclic dienes in moderate to good yields. These stereodefined dienes proved to be versatile substrates for the preparation of various polycyclic products through subsequent Diels-Alder, intramolecular Friedel-Crafts or thermal electrocyclization reactions.
1 Introduction
2 Formation of Cyclopentanic Derivatives
3 Formation of Cyclohexanic Derivatives
3.1 Synthesis of 1,3-Bis-Exocyclic Dienes
3.2 Synthesis of Conjugated Trienes
4 Synthetic Applications
4.1 Diels-Alder Reaction
4.2 Intramolecular Friedel-Crafts Reaction
4.3 Thermal Electrocyclization
4.3.1 Reaction on Conjugated Exocyclic Trienes
4.3.2 One-Pot Synthesis of Functionalized Cyclohexadienes
5 Conclusion
Key words
palladium - cyclization - enynes - exocyclic dienes - electrocyclization
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