Preparation of (E)-4-Aryl-1,1,1-trifluoro-3-tosylbut-3-en-2-ones as Fluorinated Building Blocks and Their Application in Ready and Highly Stereoselective Routes to trans-2,3-Dihydrofurans Substituted with Trifluoromethyl and Sulfonyl Groups

• Published in: European journal of organic chemistry Vol. 2012; no. 16; pp. 3142 - 3150
• Main Authors: Yu, Haigang, Han, Jing, Chen, Jie, Deng, Hongmei, Shao, Min, Zhang, Hui, Cao, Weiguo
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.06.2012; WILEY‐VCH Verlag; Wiley; Wiley-VCH
• Subjects: 2,3‐Dihydrofurans; 3-Dihydrofurans; Arsonium salts; Chemistry; Chemistry, Organic; Exact sciences and technology; Fluorine; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Organic chemistry; Oxygen heterocycles; Physical Sciences; Preparations and properties; Science & Technology; Stereoselective synthesis; Sulfones; Trifluoromethyl substituent; Ylides; ORGANIC-SYNTHESIS; Trifluoromethyl substituent; Oxygen heterocycles; VINYL SULFONES; ARSONIUM YLIDES; Fluorine; EFFICIENT SYNTHESIS; DIHYDROFURAN-FUSED PERHYDROPHENANTHRENES; RING-SYSTEMS; 3-Dihydrofurans; TETRASUBSTITUTED 2,3-DIHYDROFURANS; 2; Arsonium salts; FACILE SYNTHESIS; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; Ylides; Sulfones; Stereoselective synthesis; Organic cation; Sulfone; Furan derivatives; Oxygen heterocycle; Ylide; Stereoselectivity; Chlorocarbon; Aromatic compound; Chemical synthesis; 2,3-Dihydrofurans; Cesium carbonate; Organic bromine compounds; Quarternary arsonium compound; Cyclization; Organic fluorine compounds; Dichloromethane; Fluorine Organic compounds; Fluorination
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201200180

(E)‐4‐Aryl‐1,1,1‐trifluoro‐3‐tosylbut‐3‐en‐2‐one fluorinated building blocks were prepared through a two‐step process. Treatment of these (E)‐4‐aryl‐1,1,1‐trifluoro‐3‐tosylbut‐3‐en‐2‐ones with arsonium bromides in the presence of Cs2CO3 in CH2Cl2 at reflux resulted in highly stereoselective ring closure to provide 4‐tosyl‐5‐trifluoromethyl‐trans‐2,3‐dihydrofurans in good to excellent yields. (E)‐4‐Aryl‐1,1,1‐trifluoro‐3‐tosylbut‐3‐en‐2‐ones were prepared through a two‐step process and used as fluorinated building blocks in the stereoselective preparation of a series of 4‐tosyl‐5‐trifluoromethyl‐trans‐2,3‐dihydrofuran derivatives with the assistance of arsonium ylides.