Water‐Compatible Synthesis of 2‐Trifluoromethyl‐1, 3‐Dioxanes. Issue 48 (20th November 2018)

• Record Type: Journal Article
• Authors: Becerra‐Figueroa, Liliana; Tiniakos, Alexander F.; Prunet, Joëlle; Gamba‐Sánchez, Diego
• Is Part Of: European journal of organic chemistry. Issue 48(2018)
• Page Start: 6929
• Page End: 6932
• Publication Date: 2018-11-20
• Subjects: Water‐compatible -- Acetals -- Oxa‐Michael -- Trifluoromethyl -- Dioxanes; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201801367
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : A water‐compatible method for the diastereoselective synthesis of 2‐trifluormethyl‐1, 3‐dioxanes is described. The reaction proceeds under mild reaction conditions using simple inorganic bases; it has a very good substrate scope and can be performed with different Michael acceptors. Additionally, the reaction products can be further functionalized, showing an excellent perspective for future applications. Abstract : A simple and practical method for the diastereoselective synthesis of fluorinated dioxanes using aqueous fluoral and KOH was developed. The products were obtained with high yields and selectivities, besides they proved to be stable enough to resist further functionalization. The reaction is easily performed and well tolerated with a broad range of substrates.