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Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

ABSTRACT: The first catalytic asymmetric addition of ynamides to aliphatic and aromatic aldehydes is described. This reaction provides unprecedented access to a diverse family of N-substituted propargylic alcohols that are obtained in high yield and ee in the presence of 10 mol% of zinc triflate and N-methylephedrine. The use of apolar solvent mixtures is essential to avoid product racemization and to optimize ee's without compromising conversion.

SUBMITTER: Cook AM

PROVIDER: S-EPMC3977694 | biostudies-literature | 2014 Mar

REPOSITORIES: biostudies-literature

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Catalytic enantioselective nucleophilic addition of ynamides to aldehydes.

Cook Andrea M AM Wolf Christian C

Chemical communications (Cambridge, England) 20140212 24

The first catalytic asymmetric addition of ynamides to aliphatic and aromatic aldehydes is described. This reaction provides unprecedented access to a diverse family of N-substituted propargylic alcohols that are obtained in high yield and ee in the presence of 10 mol% of zinc triflate and N-methylephedrine. The use of apolar solvent mixtures is essential to avoid product racemization and to optimize ee's without compromising conversion. ...[more]

PMID: 24519669

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