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Alkenyl copper reagents - 18. Carbocupration of acetylenic acetals and ketals. Synthesis of manicone, geranial and 2,4-(E,Z)-dienals

Authors
Commercon, A.
Coulentianos, C.
Normant, Jean F.
Published in Tetrahedron. 1984, vol. 40, no. 4, p. 715-731
Abstract Lithium diorganocuprates add across the triple bond of substituted and non-substituted acetylenic acetals and ketals to give dialkenylcuprates, which can be decomposed into alkoxyallenes or may be trapped with a variety of electrophiles, such as alkyl, alkenyl, alkynyl and aryl halides. They may also undergo conjugate addition to a-ßunsaturated esters and ketones. The method is used for the synthesis of (±)-manicone, pure geranial and (E,Z)2,4-dienals.
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ALEXAKIS, Alexandre et al. Alkenyl copper reagents - 18. Carbocupration of acetylenic acetals and ketals. Synthesis of manicone, geranial and 2,4-(E,Z)-dienals. In: Tetrahedron, 1984, vol. 40, n° 4, p. 715-731. https://archive-ouverte.unige.ch/unige:8167

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Deposited on : 2010-06-21

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