| Autor: |
Yejin, Chang, Min, Cao, Jessica Z, Chan, Cunyuan, Zhao, Yuankai, Wang, Rose, Yang, Masayuki, Wasa |
| Rok vydání: |
2021 |
| Předmět: |
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| Zdroj: |
J Am Chem Soc |
| ISSN: |
1520-5126 |
| Popis: |
We disclose a catalytic method for β-C(sp(3))–H functionalization of N-alkylamines for synthesis of enantiomerically enriched β-substituted amines, entities prevalent in pharmaceutical compounds and used to generate different families of chiral catalysts. We demonstrate that a catalyst system comprising of seemingly competitive Lewis acids, B(C(6)F(5))(3) and a chiral Mg- or Sc-based complex, promotes the highly enantioselective union of N-alkylamines and α,β-unsaturated compounds. An array of δ-amino carbonyl compounds was synthesized under redox-neutral conditions by enantioselective reaction of a N-alkylamine-derived enamine and an electrophile activated by the chiral Lewis acid co-catalyst. The utility of the approach is highlighted by late-stage β-C–H functionalization of bioactive amines. Investigations in regard to the mechanistic nuances of the catalytic processes are described. |
| Databáze: |
OpenAIRE |
| Externí odkaz: |
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