C(sp2)−H Hydrogen‐Bond Donor Groups in Chiral Small‐Molecule Organocatalysts. Issue 8 (7th June 2019)

• Record Type: Journal Article
• Authors: Reep, Carlyn; Sun, Shiyu; Takenaka, Norito
• Is Part Of: Asian journal of organic chemistry. Volume 8:Issue 8(2019)
• Page Start: 1306
• Page End: 1316
• Publication Date: 2019-06-07
• Subjects: anion binding -- hydrogen bonding -- Lewis bases -- organocatalysis -- phase transfer; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201900122
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: Asymmetric catalysis of chemical transformations by chiral small organic molecules has become an important approach in organic synthesis. Attractive noncovalent interactions such as N(O)−H hydrogen‐bonding, π‐stacking, and cation‐π interactions have been exploited as the primary and/or secondary function(s) of the catalysts, but C( sp 2 )−H hydrogen‐bonding interactions have been underutilized in this context. This Minireview showcases selected organocatalysts in which C( sp 2 )−H hydrogen‐bonding interactions are invoked in their mechanism of catalysis, examples of which can be inspirational for the development of new catalysts. Abstract : C−H hydrogen bonding : This Minireview highlights burgeoning organocatalysts bearing C( sp 2 )−H hydrogen bond donors. The C( sp 2 )−H⋅⋅⋅X attractive interactions are more prevalent in organocatalysis than previously considered and in fact are becoming increasingly important as design elements for the development of new catalysts.