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A cheap metal for a challenging task: nickel-catalyzed highly diastereo- and enantioselective hydrogenation of tetrasubstituted fluorinated enamides† †Electronic supplementary information (ESI) available: Experimental procedures and NMR spectra of the compounds. CCDC 1845389. For ESI and crystallogr
| Content Provider | Semantic Scholar |
|---|---|
| Author | Guan, Yu-Qing Han, Zhengyu Li, Xiuxiu You, Cai Yin Tan, Xuefeng Zhang, Xumu |
| Copyright Year | 2019 |
| Abstract | Nickel-catalyzed asymmetric hydrogenation of challenging tetrasubstituted fluorinated enamides has been achieved, affording chiral α-fluoro-β-amino esters in high yields with excellent diastereo- and enantioselectivities (up to 98% yield, >99 : 1 dr, up to >99% ee). Deuterium-labeling experiments and control experiments were conducted to probe the mechanism, and the results indicated that the acidity of the solvent plays a critical role in the control of diastereoselectivity by trapping the adduct of nickel hydride to C[double bond, length as m-dash]C bonds via protonolysis, giving the hydrogenation product with stereospecific syn-selectivity. This protocol provides efficient access to chiral α-fluoro-β-amino esters which have important potential applications in organic synthesis and medicinal chemistry. |
| Starting Page | 252 |
| Ending Page | 256 |
| Page Count | 5 |
| File Format | PDF HTM / HTML |
| DOI | 10.1039/c8sc04002h |
| PubMed reference number | 30746080 |
| Journal | Medline |
| Volume Number | 10 |
| Alternate Webpage(s) | https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/06/da/SC-010-C8SC04002H.PMC6335620.pdf |
| Journal | Chemical science |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |
