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ChemInform Abstract: Enantioselective Synthesis of α-Amino Acids from Glycine t-Butyl Ester.

✍ Scribed by T.-L. YEH; C.-C. LIAO; B.-J. UANG

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis

The diastereoselective synthesis of α-amino esters from the glycine ester (I) employing the sulfonamides (II) as chiral auxiliaries works well for α-alkylation with methyl iodide. Ethylation, allylation, and benzylation proceeds with fair stereoselectivity, but pure diastereomers can be obtained by single recrystallization in good yields. The change of preferred stereoselectivity on alkylation of the glycine ester derivatives (III) is unexpected (cf. (IIIa) → (Vb) + (VIb) and (IIIa) → ( Vd) + (VId)). -(YEH, T.

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