Chiral Allylsilane Additions to Chiral alpha-Substituted Aldehydes

Chiral allylsilane 3 reacted with chiral alpha-methyl-beta-siloxy-aldehydes to afford the corresponding 1,4-syn-products with good diastereoselectivities independent of the absolute stereochemistry of these aldehydes. The best selectivities are observed when the reactions are carried out by transmet...

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Bibliographic Details
Published inJournal of the Brazilian Chemical Society Vol. 9; no. 4; pp. 357 - 369
Main Authors Dias, Luiz C., Giacomini, Rosana
Format Journal Article
LanguageEnglish
Published Sociedade Brasileira de Química 01.08.1998
Subjects
CHEMISTRY, MULTIDISCIPLINARY
transmetallation
chiral allylsilane
polyacetate derived natural products
1,4-asymmetric induction
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Summary:Chiral allylsilane 3 reacted with chiral alpha-methyl-beta-siloxy-aldehydes to afford the corresponding 1,4-syn-products with good diastereoselectivities independent of the absolute stereochemistry of these aldehydes. The best selectivities are observed when the reactions are carried out by transmetallation of the allylsilane 3 using Tin (IV) Chloride in CH2Cl2, at -78 °C, before addition of the aldehydes.
ISSN:0103-5053
1678-4790
DOI:10.1590/S0103-50531998000400008