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Catalytic enantioselective difluoroalkylation of aldehydes.
Angew Chem Int Ed Engl. 2013 Jul 22; 52(30):7869-73.AC

Abstract

Copper-catalyzed bond scission of pentafluorobutane-1,3-diones generates difluoroenolates that react with aldehydes to give a wide range of chiral α,α-difluoro-β-hydroxy ketones within a few hours in up to 99 % yield and 92 % ee. The synthetic utility of this reaction is demonstrated with the stereoselective synthesis of a chiral anti-1,3-diol exhibiting a central difluoromethylene unit and efficient conversion to a 2,2-difluoro-3-hydroxy carboxylic acid.

Authors+Show Affiliations

Department of Chemistry, Georgetown University, 37th and O Streets, Washington, DC 20057, USA.No affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23780866

Citation

Zhang, Peng, and Christian Wolf. "Catalytic Enantioselective Difluoroalkylation of Aldehydes." Angewandte Chemie (International Ed. in English), vol. 52, no. 30, 2013, pp. 7869-73.
Zhang P, Wolf C. Catalytic enantioselective difluoroalkylation of aldehydes. Angew Chem Int Ed Engl. 2013;52(30):7869-73.
Zhang, P., & Wolf, C. (2013). Catalytic enantioselective difluoroalkylation of aldehydes. Angewandte Chemie (International Ed. in English), 52(30), 7869-73. https://doi.org/10.1002/anie.201303551
Zhang P, Wolf C. Catalytic Enantioselective Difluoroalkylation of Aldehydes. Angew Chem Int Ed Engl. 2013 Jul 22;52(30):7869-73. PubMed PMID: 23780866.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic enantioselective difluoroalkylation of aldehydes. AU - Zhang,Peng, AU - Wolf,Christian, Y1 - 2013/06/18/ PY - 2013/04/25/received PY - 2013/6/20/entrez PY - 2013/6/20/pubmed PY - 2013/10/25/medline KW - aldol reaction KW - asymmetric catalysis KW - cleavage reactions KW - fluoroenolates KW - reactive intermediates SP - 7869 EP - 73 JF - Angewandte Chemie (International ed. in English) JO - Angew. Chem. Int. Ed. Engl. VL - 52 IS - 30 N2 - Copper-catalyzed bond scission of pentafluorobutane-1,3-diones generates difluoroenolates that react with aldehydes to give a wide range of chiral α,α-difluoro-β-hydroxy ketones within a few hours in up to 99 % yield and 92 % ee. The synthetic utility of this reaction is demonstrated with the stereoselective synthesis of a chiral anti-1,3-diol exhibiting a central difluoromethylene unit and efficient conversion to a 2,2-difluoro-3-hydroxy carboxylic acid. SN - 1521-3773 UR - https://www.unboundmedicine.com/medline/citation/23780866/Catalytic_enantioselective_difluoroalkylation_of_aldehydes_ L2 - https://doi.org/10.1002/anie.201303551 DB - PRIME DP - Unbound Medicine ER -