Lillo V J, Saá J M
Departamento de Química, Universidad de las Islas Baleares, 07122, Palma de Mallorca, Spain.
Chemistry. 2016 Nov 21;22(48):17182-17186. doi: 10.1002/chem.201604433. Epub 2016 Oct 18.
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.
具有协同氢键网络（NCHB）的有机催化剂已以类似酶的方式用于对映体纯的六氢嘧啶酮（HHPMs）或二氢嘧啶酮（DHPMs）的直接、可切换合成，该合成从常见的、易于获得的α-脲基砜阶段开始。即使在有机碱存在的情况下，NCHB有机催化剂也能充分发挥其作为纯氢键仿生催化剂的潜力。这种一锅法的非对映和对映选择性合成方法已被证明是稳健的、可扩展的、高效的且环境友好的。首次报道了一种直接且真正实用的制备对映体纯HHPMs的方法。
