Tang Xiaoxue, He Hualing, Fang Xiantao, Chang Zexu, Antilla Jon C
Institute for Molecular Design and Synthesis, School of Pharmaceutical Science and Technology, Health Science Platform, Tianjin University, Tianjin, China.
Chirality. 2019 Aug;31(8):592-602. doi: 10.1002/chir.23101. Epub 2019 Jun 13.
Using chiral BINOL-derived phosphoric acids (PA's) to activate substrates for enhanced reactivity is now regarded as a powerful strategy to control enantioselectivity in asymmetric synthesis. Generally, most substituents at the 3,3'-positions of BINOL PA's are aryl derivatives. These derivatives are pivotal in attaining high selectivity. PA's with alkyl substituents in these positions have rarely been reported. Herein, we introduced alkyl-based substituents at the 3,3'-position of PA's. These new potential catalysts, if applied in reactions, may allow altered noncovalent interactions (as opposed to the typical aryl substituents in these positions) with substrates used in chiral PA-catalyzed chemistry in the future.
使用手性联萘酚衍生的磷酸（PA）来活化底物以提高反应活性，如今被视为在不对称合成中控制对映选择性的一种强大策略。一般来说，联萘酚磷酸在3,3'-位的大多数取代基都是芳基衍生物。这些衍生物对于实现高选择性至关重要。在这些位置具有烷基取代基的磷酸很少被报道。在此，我们在磷酸的3,3'-位引入了基于烷基的取代基。这些新型潜在催化剂如果应用于反应中，未来可能会在手性磷酸催化的化学反应中与底物产生不同的非共价相互作用（与这些位置典型的芳基取代基不同）。
