Asymmetric synthesis of 2,4,5-substituted prolines through 1,3-dipolar addition reaction of N-arylidene menthyl esters of alpha-aminoacid with methyl acrylate

• Published in: Indian journal of chemistry. Sect. B. Organic chemistry, including medicinal chemistry Vol. 59; no. 7; pp. 1039 - 1042
• Main Authors: Prasad, Jagdish, Kumar, Munish, Panday, Sharad Kumar
• Format: Journal Article
• Language: English
• Published: NEW DELHI Natl Inst Science Communication & Information Resources-Niscair 01.07.2020
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; Schiff base; Asymmetric synthesis; X=Y-ZH SYSTEMS; CYCLOADDITIONS; 1,3-dipolar addition; CONFIGURATION; alpha-amino acid; 2,4,5-substituted prolines; AZOMETHINE YLIDES; POTENTIAL 1,3-DIPOLES; DERIVATIVES
• ISSN: 0376-4699; 0019-5103; 0975-0983
• DOI: 10.56042/ijcb.v59i7.42578

Proline and its derivatives constitute the important organic entities as organocatalyst, ACE inhibitors, bioactive molecules/intermediates to bioactive molecules as well as components of various natural products e.g. Kainic acid, (-)-domoic acid, etc. Due to its wide range of utility extensive studies have been made for the synthesis of 2, 3, 4 or 5 substituted prolines. One pot synthesis of 2,4,5-substituted prolines through 1,3-dipolar addition of various amino acids with homochiral acrylate has also been carried out successfully. Herein we wish to report the 1,3-dipolar addition of Schiff bases, where chiral auxiliary has been introduced in the Schiff bases and 1,3dipolar addition with methyl acrylate leading to the synthesis of 2(S),4(S),5(R)-substituted prolines has been achieved successfully.