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EnglishOn 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.
| Autori interni: | |
| Autori: | ANDREINI B. P; CARPITA A; ROSSI R; SCAMUZZI B |
| Titolo: | 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 |
| Anno del prodotto: | 1989 |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
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