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C( sp 2 )−H Hydrogen‐Bond Donor Groups in Chiral Small‐Molecule Organocatalysts
Author(s) -
Reep Carlyn,
Sun Shiyu,
Takenaka Norito
Publication year - 2019
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201900122
Subject(s) - chemistry , catalysis , hydrogen bond , stacking , organocatalysis , non covalent interactions , molecule , context (archaeology) , enantioselective synthesis , combinatorial chemistry , hydrogen bond catalysis , stereochemistry , organic chemistry , paleontology , biology
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.