Catalytic Asymmetric Aldol-Type Reaction of Zinc Enolate Equivalent of Amides

Treatment of phenyl isocyanate with bis(iodozincio)methane gave a zinciomethylenated product, which acts as an amide-enoate equivalent. It did not react with an aldehyde efficiently, but gave the corresponding adduct in good yield in the presence of an aminoalcohol. Use of a catalytic amount of chir...

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Bibliographic Details
Published in:Organic letters 2013-07, Vol.15 (13), p.3378-3380
Main Authors: Haraguchi, Ryosuke, Matsubara, Seijiro
Format: Article
Language:English
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Summary:Treatment of phenyl isocyanate with bis(iodozincio)methane gave a zinciomethylenated product, which acts as an amide-enoate equivalent. It did not react with an aldehyde efficiently, but gave the corresponding adduct in good yield in the presence of an aminoalcohol. Use of a catalytic amount of chiral aminoalcohol led the process to the catalytic asymmetric Aldol-type reaction.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401425s