57. Preparation and Electrophilic Substitution of 1-Trimethylsilylpentadienyllithium
    Oppolzer, W.; Burford, S. C.; Marazza, F.
    Helv. Chim. Acta 1980, 63, 555-562

Pentadienyllithium (16) was regioselectively and efficiently transformed to 1-trimethylsilyl-2,4-pentadiene (17) by reaction with chlorotrimethylsilane (Scheme 5). Deprotonation of 17 and subsequent electrophilic attack furnished the regioisomeric products 12 and/or13 in good yields (Schemes 5 and 6). The utility of the reaction 18→12 for the convergent assembly of the 1-silyl-1,3-butadiene unit with an olefinic dienophile is further illustrated by the smooth intramolecular Diels-Alder reaction 19→20.

DOI : 10.1002/hlca.19800630302