Enantioselective Alkynylation Reactions to Aldehydes: The Effects of Aromatic Substituents upon the Enantioselectivity

ABSTRACT Asymmetric alkynylation reactions to linear alkyl and substituted aromatic aldehydes have been accomplished in good yields and with a range of selectivities. For aromatic aldehydes we observed that the selectivity of the alkynylation reaction appears to depend upon the substituents on the a...

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Bibliographic Details
Published in:Synthesis (Stuttgart) 2006-09, Vol.2006 (18), p.3099-3105
Main Authors: Tyrrell, Elizabeth, Tesfa, Kibur Hunie, Millet, Julien, Muller, Christophe
Format: Article
Language:English
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Summary:ABSTRACT Asymmetric alkynylation reactions to linear alkyl and substituted aromatic aldehydes have been accomplished in good yields and with a range of selectivities. For aromatic aldehydes we observed that the selectivity of the alkynylation reaction appears to depend upon the substituents on the aromatic ring. Thus with electron-withdrawing substituents both the yield and enantioselectivities were good to excellent. In contrast to this, the presence of electron-donating groups provided excellent conversions; however, these were coupled with poor enantioselectivities.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2006-950205