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Preparation and Electrophilic Substitution of 1‐Trimethylsilylpentadienyllithium
Author(s) -
Oppolzer Wolfgang,
Burford Sidney C.,
Marazza Fabrizio
Publication year - 1980
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19800630302
Subject(s) - chemistry , electrophile , intramolecular force , silylation , deprotonation , trimethylsilyl , electrophilic substitution , substitution reaction , medicinal chemistry , organic chemistry , stereochemistry , catalysis , ion
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/or 13 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 .