Front Cover: Tris(pentafluorophenyl)borane‐Assisted Chiral Phosphoric Acid Catalysts for Enantioselective Inverse‐Electron‐Demand Hetero‐Diels‐Alder Reaction of α, β‐Substituted Acroleins (Asian J. Org. Chem. 7/2019). Issue 7 (26th June 2019)

• Record Type: Journal Article
• Authors: Hatano, Manabu; Sakamoto, Tatsuhiro; Mochizuki, Takuya; Ishihara, Kazuaki
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 7(2019)
• Page Start: 918
• Page End: 918
• Publication Date: 2019-06-26
• Subjects: [4+2] cycloaddition -- boron Lewis acid -- chiral Brønsted acid catalyst -- inverse-electron-demand hetero-Diels-Alder reaction -- phosphoric acid; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900184
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract : In our previous study, BBr3 ‐assisted chiral phosphoric acid catalysts promoted the enantioselective [2+2] cycloaddition of acroleins with phenyl vinyl sulfide [night in the picture]. In the present study, bulky B(C6 F5 )3 ‐assisted chiral phosphoric acid catalysts promoted the enantioselective inverse‐electron‐demand hetero‐Diels–Alder reaction (i.e., [4+2] cycloaddition) of acroleins with ethyl vinyl sulfide [day in the picture]. The chiral cavity of the catalysts [volcanoes in the picture], particularly with the respective use of BBr3 [Moon in the picture] and B(C6 F5 )3 [Sun in the picture], could control the enantioselectivity of the reactions. More information can be found in the Communication by Kazuaki Ishihara et al. on page 1061 in Issue 7, 2019 (DOI: 10.1002/ajoc.201900104 ).