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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Bibliographic Details
Published inOrganic letters Vol. 4; no. 26; pp. 4735 - 4737
Main Authors Spino, Claude, Granger, Marie-Claude, Tremblay, Marie-Claude
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 26.12.2002
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OBTAINING UNUSUAL EQUATORIAL
REAGENTS
ANTI-CRAM
STEREOSELECTIVE ADDITION
CARBONYL ALKYLATION
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Summary: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