BF3·OEt2-mediated nucleophilic fluorocyclization of sulfonyl 3-methylene-oxabenzocyclooctan-6-ones. Diastereocontrolled synthesis of benzofused fluorooxabicyclo[4.2.1]nonanes. Issue 37 (15th September 2022)

• Record Type: Journal Article
• Authors: Hsueh, Nai-Chen; Chang, Meng-Yang
• Is Part Of: Organic & biomolecular chemistry. Volume 20:Issue 37(2022)
• Page Start: 7503
• Page End: 7518
• Publication Date: 2022-09-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d2ob01459a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : We describe the diastereocontrolled preparation of novel sulfonyl benzofused fluorooxabicyclo[4.2.1]nonanes, including (i) NaBH4 -mediated reduction and (ii) BF3 ·OEt2 -mediated intramolecular nucleophilic fluorocyclization. Abstract : We describe a facile-operational, high-yield method for the diastereocontrolled preparation of novel sulfonyl benzofused fluorooxabicyclo[4.2.1]nonanes by a straightforward synthetic route, including (i) NaBH4 -mediated reduction of sulfonyl 3-methylene-oxabenzocyclooctan-6-ones and (ii) BF3 ·OEt2 -mediated intramolecular nucleophilic fluorocyclization. The plausible mechanism for the preparation is proposed and discussed. This protocol can easily install a fluoro-atom on the bridged head position in a short time and under mild conditions, resulting in one carbon–carbon and one carbon–fluorine bond formation.