1417600-53-3Relevant academic research and scientific papers
Synthesis of Proline Analogues via Rh-Catalyzed Asymmetric Conjugate Addition
Edelstein, Emma K.,Rankic, Danica A.,Dudley, Caroline C.,McMinn, Spencer E.,Adpressa, Donovon A.
, p. 743 - 749 (2021)
An enantio- and diastereoselective Rh-catalyzed conjugate addition reaction for the synthesis of proline analogues is reported. A high-throughput experimentation campaign was used to identify an efficient chiral catalyst which was able to afford the desired products in high yield and with high levels of diastereo- and enantioselectivity. This method was used to afford a range of 3-substituted proline derivatives from readily available dehydroproline electrophiles and boronic acid nucleophiles.
Organocatalytic michael addition of nitro esters to a,β-unsaturated aldehydes: Towards the enantioselective synthesis of trans-3-substituted proline derivatives
Han, Man-Yi,Zhang, Yong,Wang, Huai-Zhen,An, Wan-Kai,Ma, Bao-Chun,Zhang, Yuan,Wang, Wei
, p. 2635 - 2640 (2013/01/15)
A facile five-step strategy has been developed for the enantioselective synthesis of trans-3- substituted proline derivatives with high diasteroselectivity (dr>20:1) and enantioselectivity (up to 97% ee). The key step is the asymmetric organocatalytic Michael addition of nitro esters to a,β-unsaturated aldehydes, which affords the chiral Michael adducts in high yields (up to 96%) and excellent enantioselectivity (up to 99% ee) by using diaryl- ACHTUNGTRENUNGprolinol silyl ether as the organocatalyst.
