Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 127, Issue 44, Pages 15453-15456Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja053259w
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Funding
- NIGMS NIH HHS [GM 57212] Funding Source: Medline
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An Al-catalyzed enantioselective method for additions of Me2Zn and Et2Zn to alpha-ketoesters bearing aromatic, alkenyl, and alkyl substituents is disclosed. Transformations are promoted in the presence of a readily available amino acid-based ligand and afford the desired products in excellent yields and in up to 95% ee. Investigations described illustrate that the presence of a Lewis basic additive can lead to significant enhancements in efficiency and enantioselectivity. A mechanistic model that provides a rationale for such effects is provided.
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