Stereoselective Traceless Borylation–Allenation of Propargylic Epoxides: Dual Role of the Copper Catalyst. Issue 69 (24th November 2017)

• Record Type: Journal Article
• Authors: Jarava‐Barrera, Carlos; Parra, Alejandro; Amenós, Laura; Arroyo, Ana; Tortosa, Mariola
• Is Part Of: Chemistry. Volume 23:Issue 69(2017)
• Page Start: 17478
• Page End: 17481
• Publication Date: 2017-11-24
• Subjects: allenes -- boron -- copper -- epoxides -- stereoselective synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201705019
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Chiral α‐allenols are prepared with high diastereocontrol through an unprecedented and spontaneous β‐oxygen elimination of an α‐epoxy vinyl boronate. Stochiometric experiments and DFT calculations support a dual role of the copper catalyst, which orchestrates the hydroboration and the syn ‐elimination step. Abstract : Dual player : In this report, chiral α‐allenols are prepared with high diastereocontrol through an unprecedented and spontaneous β‐oxygen elimination of an α‐epoxy vinyl boronate. Stoichiometric experiments and DFT calculations support a dual role of the copper catalyst, which orchestrates the hydroboration and the syn ‐elimination step.