Rh(III)-catalyzed C–H activation-desymmetrization of diazabicycles using enol as directing group: A straightforward approach to difunctionalized cyclopentenes. Issue 14 (4th April 2018)

• Record Type: Journal Article
• Authors: Zhang, Yan; Shang, Tianbo; Li, Lisha; He, Yu; Wen, Tingting; Tu, Yanan; Wang, Shanshan; Lin, Dan
• Is Part Of: Tetrahedron letters. Volume 59:Issue 14(2018)
• Page Start: 1394
• Page End: 1397
• Publication Date: 2018-04-04
• Subjects: Rh(III)-catalysis -- C–H activation -- Cyclopentene -- Enol -- Desymmetrization; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.02.063
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Using enol as directing group. Single chemeoselectivity. Short reaction time, good to excellent yields and broad substrate scope. Small loading of catalyst and additive. Abstract: A Rh(III)-catalyzed C–H activation-desymmetrization of diazabicycles with o -vinylphenols as an efficient approach to alkenyl-substituted aminocyclopentenes is reported. This protocol represents another classic example for direct C–H activation of terminal alkenes using enol as directing group. The reaction features the ease of the preparation of starting materials, fast and high efficiency, broad substrate scope and 100% atom economy, thus provides a valuable entry to synthesize novel substituted cyclopentenes.