The Pd(II)- or Ag(I)-catalyzed lactonization of easily available (E)-4- (1-alkynyl)-2-bromopropenoic acids provides (Z)-3-bromo-5-ylidene-5H-furan- 2-ones, 5. These compounds, which represent an unpreviously reported class of (Z)-alkylidenebutenolides, are able to undergo Pd-catalyzed cross-coupling reactions with arylzinc halides, tetraalkylstannanes or alkenylstannanes to provide the corresponding 3-substituted (Z)-5-ylidene-5H-furan-2-ones, 1. The new procedure for the preparation of compounds 1 has been employed in a new synthesis of the butter flavour component bovolide.
A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones / Renzo, Rossi; Fabio, Bellina; Mannina, Luisa. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 39:19(1998), pp. 3017-3020.
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Titolo: | A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones |
Autori: | |
Data di pubblicazione: | 1998 |
Rivista: | |
Citazione: | A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones / Renzo, Rossi; Fabio, Bellina; Mannina, Luisa. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - STAMPA. - 39:19(1998), pp. 3017-3020. |
Handle: | http://hdl.handle.net/11573/42498 |
Appartiene alla tipologia: | 01a Articolo in rivista |