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Palladium‐Catalysed Isomerisation of 2‐Vinylidenehydrofurans to 1,3‐Dienes and Some Aspects of Their Reactivity
Author(s) -
Ghobsi Abdelkader,
Hacini Salih,
Wavrin Laurence,
GaudelSiri Anouk,
Corbères Agnès,
Nicolas Cyril,
Bonne Damien,
Viala Jacques,
Rodriguez Jean
Publication year - 2008
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200800517
Subject(s) - chemistry , isomerization , palladium , regioselectivity , reactivity (psychology) , catalysis , organic chemistry , combinatorial chemistry , medicine , alternative medicine , pathology
The transformation of easily accessible 2‐vinylidenehydrofurans into stable 1,3‐dienes has been achieved by using catalytic amounts of palladium(0). These valuable compounds were then engaged in subsequent Diels–Alder reactions giving access to complex heterocyclic cores found in numerous natural products. A rationale for the regioselectivity of the Diels–Alder reactions with vinylfurans has been provided by DFT calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)