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Synthesis 2007(23): 3754-3757
DOI: 10.1055/s-2007-983851
DOI: 10.1055/s-2007-983851
PSP
© Georg Thieme Verlag Stuttgart · New York
Enantioselective Addition of Dimethylzinc to α-Keto Esters
Further Information
Received
16 May 2007
Publication Date:
08 August 2007 (online)
Publication History
Publication Date:
08 August 2007 (online)
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Abstract
The readily available (+)-N-Benzyl-(S)-mandelamide catalyzes the enantioselective addition of dimethylzinc to α-keto esters to give α-methyl-α-hydroxy esters containing stereogenic quaternary centers with moderate to good yields (56-87%). A good enantioselectivity of the reaction is obtained for aryl and heteroaryl keto esters. For these substrates ee values of 75-90% are obtained. The enantioselectivity is somewhat lower for the substrates bearing an aliphatic chain.
Key words
organometallic reagents - asymmetric catalysis - addition reactions - α-keto esters - mandelamides
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References
The flask was opened and the solid reagent rapidly added.