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Synthesis of new Calpha-tetrasubstituted alpha-amino acids.

ABSTRACT: C(alpha)-Tetrasubstituted alpha-amino acids are important building blocks for the synthesis of peptidemimetics with stabilized secondary structure, because of their ability to rigidify the peptide backbone. Recently our group reported a new class of cyclic C(alpha)-tetrasubstituted tetrahydrofuran alpha-amino acids prepared from methionine and aromatic aldehydes. We now report the extension of this methodology to aliphatic aldehydes. Although such aldehydes are prone to give aldol products under the reaction conditions used, we were able to obtain the target cyclic amino acids in low to moderate yields and in some cases with good diastereoselectivity.

SUBMITTER: Grauer AA

PROVIDER: S-EPMC2649440 | biostudies-literature | 2009

REPOSITORIES: biostudies-literature

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Synthesis of new Calpha-tetrasubstituted alpha-amino acids.

Grauer Andreas A AA König Burkhard B

Beilstein journal of organic chemistry 20090218

C(alpha)-Tetrasubstituted alpha-amino acids are important building blocks for the synthesis of peptidemimetics with stabilized secondary structure, because of their ability to rigidify the peptide backbone. Recently our group reported a new class of cyclic C(alpha)-tetrasubstituted tetrahydrofuran alpha-amino acids prepared from methionine and aromatic aldehydes. We now report the extension of this methodology to aliphatic aldehydes. Although such aldehydes are prone to give aldol products under ...[more]

PMID: 19259341

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