Towards Enzyme-like, Sustainable Catalysis: Switchable, Highly Efficient Asymmetric Synthesis of Enantiopure Biginelli Dihydropyrimidinones or Hexahydropyrimidinones.
Organocatalysts displaying a network of cooperative hydrogen bonds (NCHB) have been employed in an enzyme-like manner for a direct, switchable synthesis of enantiopure hexahydropyrimidinones (HHPMs) or dihydropyrimidinones (DHPMs), which starts at a common, easily accessible α-ureidosulfone stage. The NCHB organocatalyst exploits all its potential as a pure hydrogen-bond biomimetic catalyst even in the presence of organic bases. This one-pot, diastereo- and enantioselective synthetic procedure has been proven to be robust, scalable, highly efficient, and environmentally benign. A straightforward and truly practical entry to enantiopure HHPMs is reported for the first time.
Departamento de Química, Universidad de las Islas Baleares, 07122, Palma de Mallorca, Spain.
V J
http://orcid.org/0000-0003-3318-3571
VJ
Lillo
Departamento de Química, Universidad de las Islas Baleares, 07122, Palma de Mallorca, Spain.
J M
http://orcid.org/0000-0001-7365-6690
JM
Saá
dihydropyrimidinones; enantioselectivity; hexahydropyrimidinones; organocatalysis; sustainable chemistry