D-Proline

• CAT Number: R048845
• CAS Number: 344-25-2
• Molecular Formula: C5H9NO2
• Molecular Weight: 115.132
• Purity: ≥95%
• Storage: -20°C
• IUPAC Name: (2R)-pyrrolidine-2-carboxylic acid
• InChI: InChI=1S/C5H9NO2/c7-5(8)4-2-1-3-6-4/h4,6H,1-3H2,(H,7,8)/t4-/m1/s1
• InChIKey: ONIBWKKTOPOVIA-SCSAIBSYSA-N
• SMILES: C1CC(NC1)C(=O)O

D-Proline (CAS 344-25-2) is a key starting material in the total synthesis of (−)-secu′amamine A and (R)-harmicine.
It can be used as a ligand for the synthesis of chiral polyoxometalate (POM) clusters. It can also be used as a catalyst in the enantioselective α-aminoxylation of aldehydes.

Reference

1.Liu, Peng, Sungwoo Hong, and Steven M. Weinreb. "Total Synthesis of the Securinega Alkaloid (−)-Secu’amamine A." Journal of the American Chemical Society 130.24 (2008): 7562-7563.
2.An, Hai‐Yan, et al. "Chiral 3D architectures with helical channels constructed from polyoxometalate clusters and copper–amino acid complexes." Angewandte Chemie International Edition 45.6 (2006): 904-908.
3.Lood, Christopher S., and Ari MP Koskinen. "Synthesis of (S)-and (R)-harmicine from proline: An approach toward tetrahydro-β-carbolines." Eur. J. Org. Chem 2014 (2014): 2357-2364.
4.Zhong, Guofu. "A facile and rapid route to highly enantiopure 1, 2‐diols by novel catalytic asymmetric α‐aminoxylation of aldehydes." Angewandte Chemie 115.35 (2003): 4379-4382.