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Synthesis of Donor–Acceptor Alkynylcyclopropanes by Diastereoselective Cyclopropanation of Electron-Deficient Alkenes with Alkoxyalkynyl Fischer Carbene Complexes

✍ Scribed by José Barluenga; Manuel A. Fernández-Rodríguez; Patricia García-García; Enrique Aguilar; Isabel Merino

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
193 KB
Volume
12
Category
Article
ISSN
0947-6539

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✦ Synopsis

Abstract

The reaction of electron‐deficient alkenes with alkoxyalkynyl Fischer carbene complexes (FCCs) represents a straightforward route to a new type of captodative (donor–acceptor) alkynylcyclopropanes, which have been prepared in moderate to high yields and in a diastereoselective manner. Some studies regarding the employment of additives to facilitate the recovery of the metal moiety after the reaction are also described. Finally, the first example of a cyclopropanation reaction through employing Fischer carbene complexes under microwave irradiation is presented; this method proved to be an advantageous alternative to the thermal reaction.

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Synthesis of Donor—Acceptor Alkynylcyclo
Synthesis of Donor—Acceptor Alkynylcyclopropanes by Diastereoselective Cyclopropanation of Electron-Deficient Alkenes with Alkoxyalkynyl Fischer Carbene Complexes.
✍ Jose Barluenga; Manuel A. Fernandez-Rodriguez; Patricia Garcia-Garcia; Enrique A 📂 Article 📅 2006 🏛 John Wiley and Sons ⚖ 23 KB 👁 1 views

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Synthesis of Indolizines and Benzoindoli
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## Abstract The formal [3+2] dipolar cycloaddition (or annulation) of donor‐acceptor cyclopropanoate esters with pyridines and 5‐nitroquinoline is reported. Electron‐deficient pyridine dipolarophiles (R=CN, CO~2~Et, COMe) participate in the annulation whereas electron rich species do not. The produ