Asymmetric Synthesis of 3-Substituted Proline Chimeras Bearing Polar Side Chains of Proteinogenic Amino Acids
- 16 October 2004
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (23) , 7940-7948
- https://doi.org/10.1021/jo048762q
Abstract
The amino-zinc-ene-enolate cyclization reaction is a straightforward route to the synthesis of 3-substituted prolines. Herein we report the application of this reaction to the syntheses of proline chimeras of lysine, glutamic acid, glutamine, arginine, and serine. All these compounds were obtained in enantiomerically pure form and suitably protected for peptide synthesis.Keywords
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