ChemInform Abstract: Transition Metal/Base-Catalyzed Aldol Reactions of Isocyanoacetic Acid Derivatives with Prochiral Ketones, a Straightforward Approach to Stereochemically Defined β,β-Disubstituted-β-hydroxy-. alpha.-amino Acids. Scope and Limitations.
✍ Scribed by V. A. SOLOSHONOK; A. D. KACHAROV; D. V. AVILOV; K. ISHIKAWA; N. NAGASHIMA; T. HAYASHI
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 39 KB
- Volume
- 28
- Category
- Article
- ISSN
- 0931-7597
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✦ Synopsis
Transition Metal/Base-Catalyzed Aldol Reactions of Isocyanoacetic Acid Derivatives with Prochiral Ketones, a Straightforward Approach to Stereochemically Defined β,β-Disubstituted-β-hydroxy-. alpha.amino Acids. Scope and Limitations.
-Methyl isocyanoacetate (II) undergoes aldol type reactions with prochiral ketones under metal/basecatalysis leading to oxazoline derivatives which can be hydrolyzed to furnish β-hydroxy-α-aminoacids (e.g. (XII)), important compounds for the de novo design of peptides and peptidomimetics. The stereochemical outcome of these ring formations is found to be influenced by the steric demand of the ketone substituents, by electrostatic interactions and in some cases by the nature of the catalyst.