An efficient and stereoselective synthetic approach to a variety of amides and nitriles with a branched and conjugated dienyne structure has been developed, starting from a readily available mono-silylated unsaturated amide and nitrile with an enyne structure. A nucleophilic hydrohalogenation of the triple bond of the enynes with NaI afforded a Z,E-iododienamide and a Z,E-iododienenitrile that, subjected to palladium-catalyzed cross-coupling reactions with a variety of terminal alkynes, led directly to the title compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.

A convenient synthesis of amides and nitriles with a branched and conjugated dienyne structure

BABUDRI, Francesco;PUNZI, Angela
2002

Abstract

An efficient and stereoselective synthetic approach to a variety of amides and nitriles with a branched and conjugated dienyne structure has been developed, starting from a readily available mono-silylated unsaturated amide and nitrile with an enyne structure. A nucleophilic hydrohalogenation of the triple bond of the enynes with NaI afforded a Z,E-iododienamide and a Z,E-iododienenitrile that, subjected to palladium-catalyzed cross-coupling reactions with a variety of terminal alkynes, led directly to the title compounds. (C) 2002 Elsevier Science Ltd. All rights reserved.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11586/125616
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