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, 9. 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-ylideng-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. (C) 1998 Elsevier science Ltd. All rights reserved.
A novel protocol for the stereoselective synthesis of variously substituted (Z)-5-ylidene-5H-furan-2-ones
ROSSI, RENZO;BELLINA, FABIO;
1998-01-01
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, 9. 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-ylideng-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. (C) 1998 Elsevier science Ltd. All rights reserved.File in questo prodotto:
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