Synthesis of N-aryl β-amino acid derivatives via Cu(ii)-catalyzed asymmetric 1,4-reduction in airElectronic supplementary information (ESI) available: Spectral, analytical data for all substrates and chiral products. See DOI: 10.1039/c9ra01203f

• Main Authors: Li, Min, Xia, Hong-Feng, Yang, Li-Yao, Hong, Tao, Xie, Lin-Jie, Li, Shijun, Wu, Jing
• Format: Journal Article
• Published: 20.03.2019
• ISSN: 2046-2069
• DOI: 10.1039/c9ra01203f

In the presence of the inexpensive and stable stoichiometric reductant polymethylhydrosiloxane (PMHS) as well as certain amounts of appropriate alcohol and base additives, the non-precious metal copper-catalyzed asymmetric 1,4-hydrosilylation of β-aryl or β-alkyl-substituted N -aryl β-enamino esters was well realized to afford a diverse range of N -aryl β-amino acid esters in high yields and excellent enantioselectivities (26 examples, 90-98% ee). This approach tolerated the handling of both catalyst and reactants in air without special precautions. The chiral products obtained have been successfully converted to the corresponding enantiomerically enriched β-lactam and unprotected β-amino acid ester, which highlighted the synthetic utility of the developed catalytic procedure. Non-precious metal copper-catalyzed asymmetric 1,4-hydrosilylation of β-aryl or β-alkyl-substituted N -aryl β-enamino esters proceeded in air in high yields and excellent enantioselectivities (26 examples, 90-98% ee).