ChemInform Abstract: Synthesis of Highly Functionalized Amino Acid and Hydroxy Acid Derivatives from γ-Aminoalkyl-Substituted α-Methylene-γ-butyrolactones.
✍ Scribed by Steffen Steurer; Joachim Podlech
- Publisher
- John Wiley and Sons
- Year
- 2010
- Weight
- 43 KB
- Volume
- 33
- Category
- Article
- ISSN
- 0931-7597
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Aminoalkyl-Substituted α-Methylene-γ-butyrolactones from α-Amino Acids Using an Indium-Mediated Barbier Allyl Addition. α-Amino aldehydes, prepared from α-amino acids, can be cleanly transformed into esters of type (III) in high yields and without racemization by In-induced Barbier reaction. The di
Efficient Synthesis of γ-Oxo-and γ-Hydroxy-α-amino Acids. -Reduction of aminoester (Va) with Zn(BH 4 ) 2 permits intermediate isolation of the γ-hydroxy derivative, which is converted to lactone (IX) during silica gel chromatography. -(MERLA, B.;
Facile Stereoselective Synthesis of γ-Substituted γ-Amino Acids from the Corresponding α-Amino Acids. -The mild and short procedure presented is compatible with common side-chain protecting groups, sensitive functionalities and preserves the chirality of the starting α-amino acid.
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