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ChemInform Abstract: Cyclopropyl Building Blocks for Organic Synthesis. Part 43. Ring Opening of Methylenecyclopropane Moieties in the Palladium-Catalyzed Cross-Coupling of Methylenecyclopropyl Bromides with Metalated CH-Acidic Compounds.

✍ Scribed by M. BRANDL; S. I. KOZHUSHKOV; S. BRAESE; A. DE MEIJERE

Publisher: John Wiley and Sons
Year: 2010
Weight: 33 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199826093

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✦ Synopsis

Cyclopropyl Building Blocks for Organic Synthesis. Part 43. Ring Opening of Methylenecyclopropane Moieties in the Palladium-Catalyzed Cross-Coupling of Methylenecyclopropyl Bromides with Metalated CH-Acidic Compounds.

-The title reactions are found to proceed with opening of the three-membered ring in analogy to the cyclopropylmetal to allylmetal ring opening. Compound (Va) is transformed into a new potentially interesting amino acid (VI) incorporating a cyclopropylidenepropenyl substituent.

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Ring Opening of Methylenecyclopropane Mo

Ring Opening of Methylenecyclopropane Moieties in the Palladium-Catalyzed Cross-Coupling of Methylenecyclopropyl Bromides with Metallated CH-Acidic Compounds

✍ Melanie Brandl; Sergei I. Kozhushkov; Stefan Bräse; Armin de Meijere 📂 Article 📅 1998 🏛 John Wiley and Sons 🌐 English ⚖ 373 KB 👁 1 views

Palladium-catalyzed cross-coupling reactions of bromo-case, to give the corresponding dienyl-substituted CH-acidic compounds 5Ϫ7 in moderate to good yields. On the other (methylenecyclopropanes) 1c, 2c with the sodium enolate of dimethyl malonate 4a and the chlorozinc enolates of the gly-hand, coupl