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ChemInform Abstract: Functionalized Carbocyclic Rings via Intramolecular Diels—Alder Reactions of in situ Generated, γ Substituted, Heteroatom-Stabilized Allyl Cations in Acidic Polar Media.

✍ Scribed by Paul A. Grieco; Michael D. Kaufman

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 30
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199916109

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✦ Synopsis

Functionalized Carbocyclic Rings via Intramolecular Diels-Alder Reactions of in situ Generated, γ Substituted, Heteroatom-Stabilized Allyl Cations in Acidic Polar Media.

-Slow addition of substrates such as (I) and (III) to a solution of lithium perchlorate and catalytic TFA generates oxygen stabilized allyl cations which undergo intramolecular Diels-Alder reaction. Tricyclic ketones (II) and (IV) are isolated in good yields. Interestingly, prolonged treatment of the product (IV) leads to a mixture of the tetracycles (V) and (VI). -(GRIECO,

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ChemInform Abstract: Carbocyclic Ring Construction via an Intramolecular Diels—Alder Reaction of an in situ-Generated, Heteroatom-Stabilized Allyl Cation: Total Synthesis of (.+-.)-Lycopodine.

✍ P. A. GRIECO; Y. DAI 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 38 KB 👁 1 views

Carbocyclic Ring Construction via an Intramolecular Diels-Alder Reaction of an in situ-Generated, Heteroatom-Stabilized Allyl Cation: Total Synthesis of (±)-Lycopodine. -The title compound (X) is totally synthesized using a [4 + 2] cycloaddition leading to the tricyclic compound (VI) possessing all