Details

Autor(en) / Beteiligte

• Petakamsetty, Ramu
• Ansari, Anas
• Ramapanicker, Ramesh

Titel

Diastereoselective synthesis of furanose and pyranose substituted glycine and alanine derivatives via proline-catalyzed asymmetric α-amination of aldehydes

Ist Teil von

• Carbohydrate research, 2016-11, Vol.435, p.37-49

Ort / Verlag

Netherlands: Elsevier Ltd

Erscheinungsjahr

2016

Quelle

MEDLINE

Beschreibungen/Notizen

• A concise organocatalytic route toward the synthesis of furanose and pyranose substituted glycine and alanine derivatives is reported. These compounds are core structural units of some of the naturally available antibiotics and antifungal agents. Proline-catalyzed asymmetric α-amination of aldehydes derived from sugars is used as the key reaction to synthesize twelve sugar amino acid derivatives. The asymmetric transformations proceeded in good yields and with good to excellent diastereoselectivity. The application of the synthesized amino acids is demonstrated by synthesizing a tripeptide containing one of them. [Display omitted] •Synthesis of sugar amino acids.•Asymmetric organocatalysis.•α-Amination of aldehydes catalyzed by proline.•Use of dialdose derivatives.