On the basis of the observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prep. nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes, (E)-1-trimethylsilyl-1-alken-3-ynes (I), (1E, 5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (II), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (III) from stereoisomeric mixts. of alkenyl bromides.  Compds. I have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (IV) by selective hydrometallations, followed by hydrolysis.  Some synthetic applications of compds. I-IV have been also examd.

Palladium-catalyzed diastereoselective syntheses of (E)-1-trimethylsilyl-2-alkenes, (E)-1-trimethylsilyl-1-alken-3-ynes, (1E,5E)-1-trimethylsilyl-1,5-alkadien-3-ynes, (1E,3Z)- and (1E,3E)-1-trimethylsilyl-1,3-alkadienes

CARPITA, ADRIANO;ROSSI, RENZO;
1989

Abstract

On the basis of the observation that (E)-1-bromo-1-alkenes undergo preferentially stereospecific Pd-catalyzed cross-couplings with a variety of organometallics, in the presence of the corresponding (Z)-stereoisomers, efficient and convenient diastereoselective procedures have been developed to prep. nearly stereoisomerically pure (E)-1-trimethylsilyl-2-alkenes, (E)-1-trimethylsilyl-1-alken-3-ynes (I), (1E, 5E)-1-trimethylsilyl-1,5-alkadien-3-ynes (II), and (1E,3E)-1-trimethylsilyl-1,3-alkadienes (III) from stereoisomeric mixts. of alkenyl bromides.  Compds. I have been stereoselectively converted into (1E,3Z)-1-trimethylsilyl-1,3-dienes (IV) by selective hydrometallations, followed by hydrolysis.  Some synthetic applications of compds. I-IV have been also examd.
ANDREINI B., P; Carpita, Adriano; Rossi, Renzo; Scamuzzi, B.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11568/12223
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