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2005
Organo-silicon compounds
S 0060
Stereochemistry of the Reaction of Si-Phenyl Silenes with Butadienes: Elaboration
the Silacycloadducts to Provide a Novel Route to Substituted Lactones. —
04- 181 of
Treatment of silyl alcohols like (I) and (XVII) under modified Peterson olefination
conditions provides access to the corresponding silenes which subsequently undergo
cycloaddition to various dienes (II), (VII) and (XII) to give the [4 + 2] adducts (III),
(VIII)/(IX), (XII)/(XIV) and (XVII), resp., in moderate to good diastereoselectivity.
Main side reactions are [2 + 2] cycloaddition, silene dimerization and ene reaction. A
Fleming—Tamao oxidation—lactonization sequence provides access to diastereomeric δ-lactones with varying substitution patterns. — (SANGANEE, M. J.; STEEL*,
P. G.; WHELLIGAN, D. K.; Org. Biomol. Chem. 2 (2004) 16, 2393-2402; Dep.
Chem., Univ. Durham, Durham DH1 3LE, UK; Eng.) — Mischke
2005
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