Synthesis of Non-proteinogenic Amino-Acid Methyl Esters with Acid-Sensitive Side Chains from a Chiral Glycine Derivative

Authors

  • Matthias Hoffmann
  • Dieter Seebach

DOI:

https://doi.org/10.2533/chimia.1997.90

Abstract

A superior chiral glycine derivative 1 (tert-butyl 2-(tert-butyl)-4-methoxy-2,5-dihydro-1,3-imidazole-1-carboxylate, BDI) for the synthesis of acid-sensitive and highly hindered α-amino-acid methyl esters is readily available by resolution methods. The heterocycle 1 is alkylated once and twice in the 5-position with very high diastereoselectivity, and the resulting products (2, 3) are hydrolyzed under very mild conditions to give methyl esters of the corresponding amino acids (610).

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Published

1997-03-26

Issue

Section

Scientific Articles