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. [10.1016/s0040-4039(98)00322-0]

A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones

MANNINA, LUISA
1998

Abstract

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.
1998
stereoselective synthesis; ylidene
01 Pubblicazione su rivista::01a Articolo in rivista
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. [10.1016/s0040-4039(98)00322-0]
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11573/42498
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