Diastereoselective synthesis of furanose and pyranose substituted glycine and alanine derivatives via proline-catalyzed asymmetric α-amination of aldehydes.
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.
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
Ramu
R
Petakamsetty
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.
Anas
A
Ansari
Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India. Electronic address: rameshr@iitk.ac.in.
Ramesh
R
Ramapanicker
D000409:Alanine / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D000586:Amination; D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry; D005998:Glycine / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000447:Aldehydes; D000606:Amino Sugars; D005663:Furans; D011714:Pyrans; D000409:Alanine; D005998:Glycine
Asymmetric amination; Dialdose; Diastereoselectivity; Organocatalysis; Sugar amino acids