Diastereoselective Au-Catalyzed Allene Cycloisomerizations to Highly Substituted Cyclopentenes

• Published in: Organic letters Vol. 19; no. 13; pp. 3394 - 3397
• Main Authors: Reeves, Ryan D, Phelps, Alicia M, Raimbach, William A. T, Schomaker, Jennifer M
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 07.07.2017; Amer Chemical Soc
• Subjects: Alkadienes; Chemistry; Chemistry, Organic; Cyclopentanes; Gold - chemistry; Molecular Structure; Physical Sciences; Science & Technology; Stereoisomerism; GOLD; DESIGN; DICARBONYL-COMPOUNDS; CHIRALITY TRANSFER; 5-ENDO-DIG CARBOCYCLIZATION; COMPLEXES; COPPER; DERIVATIVES; CYCLIZATION; CONIA-ENE REACTION

Site- and regiocontrolled Au-catalyzed allene carbocyclizations furnish highly substituted cyclopentenes in >1:1 dr. Significant substitution on the substrate is tolerated, with potential to install five contiguous stereocenters after alkene functionalization. Major challenges include identifying...