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Synthesis of N-aryl β-amino acid derivatives via Cu(ii)-catalyzed asymmetric 1,4-reduction in air

Author:
Li, Min, Xia, Hong-Feng, Yang, Li-Yao, Hong, Tao, Xie, Lin-Jie, Li, Shijun, Wu, Jing
Source:
RSC advances 2019 v.9 no.16 pp. 9187-9192
ISSN:
2046-2069
Subject:
additives, air, amino acids, beta-lactams, catalysts, copper, enantioselectivity, esters, reducing agents
Abstract:
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.
Agid:
6345117