期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 24, 期 36, 页码 8994-8998出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801670
关键词
allylic alkylations; enantioselectivity; homogeneous catalysis; Morita-Baylis-Hillman adducts; tertiary fluoro-enolates
资金
- National Natural Science Foundation of China [21472082, 21772085, 21761132021]
- IKERBASQUE, Basque Foundation for Science
Owing to the innovative applications of fluorinated compounds in many areas of technology and medicine, methods for the preparation of C-F quaternary fluorine containing compounds are in extremely high demand. Here, we report the discovery of a general procedure for an S(N)2 reaction catalyzed by Pd/Ding-SKP-type ligands, and that occurs between Colby pro-enolates with MBH carbonates to afford the corresponding products featuring two consecutive stereogenic carbons, including a C-F quaternary stereogenic center. The reactions readily occur at ambient temperatures with high chemical yields and in excellent chemo-, diastereo- and enantioselective manners. This practically attractive stereochemical outcome, coupled with the operational simplicity and structural generality, bodes well for the synthetic application of this process in the preparation of a novel class of biologically relevant fluorine-containing compounds.
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