Increased Felkin−Anh Selectivity Using AlMe3 in the Addition of Vinyllithiums to α-Chiral Aldehydes:  Do “Ate” Complexes Play Any Role?

Increased Felkin−Anh Selectivity Using AlMe3 in the Addition of Vinyllithiums to α-Chiral Aldehydes:  Do “Ate” Complexes Play Any Role?

AlMe3 dramatically increases the diastereoselectivity of addition of vinyllithiums to α-chiral aldehydes but decreases that of methyllithium. Our results are explained in terms of an addition of the free vinyllithium on the Me3Al−aldehyde complex.

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Veröffentlicht in:Organic letters 2002-12, Vol.4 (26), p.4735-4737
Hauptverfasser: Spino, Claude, Granger, Marie-Claude, Tremblay, Marie-Claude
Format: Artikel
Sprache:eng
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Zusammenfassung:AlMe3 dramatically increases the diastereoselectivity of addition of vinyllithiums to α-chiral aldehydes but decreases that of methyllithium. Our results are explained in terms of an addition of the free vinyllithium on the Me3Al−aldehyde complex.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol027236n