Volume 24, Issue 32
Isocyclic Compounds
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ChemInform Abstract: Palladium-Catalyzed Intramolecular Alkyne-Carbon Monoxide-Alkene Insertion Cascade for Synthesis of α-Methylenecyclopentenones.

N. C. IHLE

N. C. IHLE

Dep. Chem., Univ. California, Berkeley, CA 94720, USA

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C. H. HEATHCOCK

C. H. HEATHCOCK

Dep. Chem., Univ. California, Berkeley, CA 94720, USA

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First published: August 10, 1993

Abstract

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ChemInform Abstract

Allylation of the propargylmalonate (I) with the chloroalkenyl acetates (II) gives the enynes (III) which are subjected to carbonylation cyclization reaction, forming the bicyclic α- methylenehexahydropentalenes (V). The latter sequence is also applied to the enynes (IX), obtained from (VI) as outlined in the reaction scheme, to give the pentalenes (X).

chemical structure image

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