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Tetraalkylammonium Salts as Hydrogen‐Bonding Catalysts
Author(s) -
Shirakawa Seiji,
Liu Shiyao,
Kaneko Shiho,
Kumatabara Yusuke,
Fukuda Airi,
Omagari Yumi,
Maruoka Keiji
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201508659
Subject(s) - catalysis , hydrogen bond , chemistry , salt (chemistry) , inorganic chemistry , hydrogen , ammonium , hydrogen bond catalysis , titration , molecule , organic chemistry , organocatalysis , enantioselective synthesis
Although the hydrogen‐bonding ability of the α hydrogen atoms on tetraalkylammonium salts is often discussed with respect to phase‐transfer catalysts, catalysis that utilizes the hydrogen‐bond‐donor properties of tetraalkylammonium salts remains unknown. Herein, we demonstrate hydrogen‐bonding catalysis with newly designed tetraalkylammonium salt catalysts in Mannich‐type reactions. The structure and the hydrogen‐bonding ability of the new ammonium salts were investigated by X‐ray diffraction analysis and NMR titration studies.