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

✍ Scribed by Melanie Brandl; Sergei I. Kozhushkov; Stefan Bräse; Armin de Meijere

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
373 KB
Volume
1998
Category
Article
ISSN
1434-193X

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✦ Synopsis

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, coupling of bicyclopropylidenylzinc chloride (2d) with diethyl bromomalonate (4e) and the electrophilic glycine cine equivalent (diphenylmethyleneamino)acetate 4c and diethyl malonate 4d, respectively, have been found to equivalent ethyl 2-acetoxy-2-(diphenylmethyleneamino)acetate (4f) gave 7 and 6 in 27 and 29% yield, respectively. proceed with opening of the three-membered ring in each

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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.
✍ M. BRANDL; S. I. KOZHUSHKOV; S. BRAESE; A. DE MEIJERE 📂 Article 📅 2010 🏛 John Wiley and Sons ⚖ 33 KB 👁 1 views

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