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Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions.
Angew Chem Int Ed Engl. 2015 May 11; 54(20):6019-23.AC

Abstract

A Cu-catalyzed asymmetric detrifluoroacetylative aldol addition reaction of 2-fluoro-1,3-diketones/hydrates to aldehydes in the presence of base and chiral bidentate ligand was developed. The reaction was carried out under convenient conditions and tolerated a wide range of substrates, resulting in fluorinated quaternary stereogenic α-fluoro-β-hydroxy ketone products with good chemical yields, diastereo- and enantioselectivities. This catalytic asymmetric detrifluoroacetylative aldol addition reaction provides a new approach for the preparation of biologically relevant products containing C-F quaternary stereogenic centers.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Xie C
School of Chemistry and Chemical Engineering, State Key Laboratory of Coordination Chemistry, Nanjing University, 22 Hankou Road, Nanjing, 210093 (China).
Wu L
No affiliation info available
Han J
No affiliation info available
Soloshonok VA
No affiliation info available
Pan Y
No affiliation info available

MeSH

AldehydesCatalysisCopperHalogenationHydrocarbons, FluorinatedKetonesModels, MolecularMolecular StructureOrganometallic Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25808758

Citation

Xie, Chen, et al. "Assembly of Fluorinated Quaternary Stereogenic Centers Through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions." Angewandte Chemie (International Ed. in English), vol. 54, no. 20, 2015, pp. 6019-23.
Xie C, Wu L, Han J, et al. Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions. Angew Chem Int Ed Engl. 2015;54(20):6019-23.
Xie, C., Wu, L., Han, J., Soloshonok, V. A., & Pan, Y. (2015). Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions. Angewandte Chemie (International Ed. in English), 54(20), 6019-23. https://doi.org/10.1002/anie.201500908
Xie C, et al. Assembly of Fluorinated Quaternary Stereogenic Centers Through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions. Angew Chem Int Ed Engl. 2015 May 11;54(20):6019-23. PubMed PMID: 25808758.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Assembly of Fluorinated Quaternary Stereogenic Centers through Catalytic Enantioselective Detrifluoroacetylative Aldol Reactions. AU - Xie,Chen, AU - Wu,Lingmin, AU - Han,Jianlin, AU - Soloshonok,Vadim A, AU - Pan,Yi, Y1 - 2015/03/24/ PY - 2015/01/30/received PY - 2015/03/01/revised PY - 2015/3/27/entrez PY - 2015/3/27/pubmed PY - 2016/2/11/medline KW - CC bond cleavage KW - aldol reaction KW - asymmetric catalysis KW - detrifluoroacetylation KW - fluorinated quaternary stereocenters SP - 6019 EP - 23 JF - Angewandte Chemie (International ed. in English) JO - Angew Chem Int Ed Engl VL - 54 IS - 20 N2 - A Cu-catalyzed asymmetric detrifluoroacetylative aldol addition reaction of 2-fluoro-1,3-diketones/hydrates to aldehydes in the presence of base and chiral bidentate ligand was developed. The reaction was carried out under convenient conditions and tolerated a wide range of substrates, resulting in fluorinated quaternary stereogenic α-fluoro-β-hydroxy ketone products with good chemical yields, diastereo- and enantioselectivities. This catalytic asymmetric detrifluoroacetylative aldol addition reaction provides a new approach for the preparation of biologically relevant products containing C-F quaternary stereogenic centers. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/25808758/Assembly_of_Fluorinated_Quaternary_Stereogenic_Centers_through_Catalytic_Enantioselective_Detrifluoroacetylative_Aldol_Reactions_ DB - PRIME DP - Unbound Medicine ER -