Intramolecular Diels–Alder reaction of cyclopenta-1,3-diene derivatives generated in situ from 4-(pent-4-enyl)cyclopent-2-enone ethylene ketals

Abstract

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Click Chemistry with Cyclopentadiene

“…Tsuji and co-workers observed that Diels–Alder reactions of 2-alkoxycyclopentadienes do not form a mixture of isomeric cycloadducts. − By incorporating an alkoxy functional group at the 2-position, Tsuji and co-workers were able to trap the cycloadducts of 5-substituted cyclopentadienes via intramolecular cycloaddition with a doubly activated dienophile to form the tricyclo­[5.2.1.0 1,5 ]­decane scaffold, as shown in Scheme . Gleason showed that incorporating a silyl ether at the 2-position of a cyclopentadiene increased the half-life of a 5-substituted cyclopentadiene from ∼1 h at 20 °C to ∼37 h at 23 °C (Scheme ).…”

A Cascade Suzuki–Miyaura/Diels–Alder Protocol: Exploring the Bifunctional Utility of Vinyl Bpin

“…5 As a result, considerable research has been focused on the generation and in situ applications of specific dienes. [6][7][8][9][10][11][12][13][14][15] Cross-coupling reactions are effective methods for the preparation of dienes for in situ DA reactions. [13][14][15] For example, Padwa reported a cascade Stille/intramolecular DA to form complex tetracyclic fused ring systems (Scheme 1, a).…”