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Title: A Chiral Nonracemic Enolate with Dynamic Axial Chirality: Direct Asymmetric Alkylation of α-Amino Acid Derivatives (SYNTHETIC ORGANIC CHEMISTRY-Fine Organic Synthesis)
Authors: Kawabata, Takeo
Suzuki, Hideo
Nagae, Yoshikazu
Chen, Jianyong
Fuji, Kaoru
Keywords: chiral enolate
dynamic chirality
asymmetric synthesis
amino acid
axial chirality
Issue Date: Mar-2001
Publisher: Institute for Chemical Research, Kyoto University
Journal title: ICR annual report
Volume: 7
Start page: 36
End page: 37
Abstract: The structure of enolate was long believed to be achiral. However, a chiral nonracemic enolate with a racemization barrier of 16 kcal/mol at -78 oC was found to be the crucial intermediate for the asymmetric -methylation of 1 to give 2 in 81% ee and 96% yield. The asymmetric -methylation occurs in other amino acid derivatives (Val, Leu, Trp, His, Tyr, Dopa) in 78-93% ee.
Appears in Collections:Vol.7 (2000)

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