手性磷酸是重要的手性Brønsted酸不對稱合成催化劑。其具有較強(qiáng)酸性,是雙功能催化劑,能通過微調(diào)結(jié)構(gòu)控制反應(yīng)立體選擇性。它可高效催化多種不對稱反應(yīng)[1-6],如Friedel–Crafts反應(yīng)、Mannich反應(yīng)、不對稱氫轉(zhuǎn)移反應(yīng)、環(huán)加成反應(yīng)等,在立體構(gòu)型上有很好的選擇性。手性磷酸的發(fā)展為手性化合物合成提供了有力手段,推動了藥物研發(fā)等領(lǐng)域的發(fā)展。
為助力相關(guān)研究,本次特別推出包含5種優(yōu)勢催化劑結(jié)構(gòu)的手性磷酸試劑盒,這些催化劑在一些反應(yīng)中均已表現(xiàn)出優(yōu)異的催化活性與選擇性。以下為其部分應(yīng)用實(shí)例:

手性磷酸(CAS: 791616-63-2)作為催化劑,以2-芳基吲哚啉為可回收氫供體,可高效實(shí)現(xiàn)酮亞胺不對稱轉(zhuǎn)移氫化反應(yīng)[7];以2-氘代苯并噻唑啉為氘供體,可實(shí)現(xiàn)酮亞胺和α-亞胺酯的不對稱轉(zhuǎn)移氘代反應(yīng)[8]。

手性磷酸(CAS: 791616-62-1)可催化的烯酮二硫縮醛不對稱質(zhì)子化反應(yīng),實(shí)現(xiàn)外消旋α-芳基氫化香豆素衍生物的去消旋化[9]。

手性磷酸(CAS: 699006-54-7)可用于α-取代丙烯醛與1,2-二氫吡啶的高對映選擇性Diels-Alder反應(yīng),生成具有高對映選擇性的異奎寧環(huán)[10]。
手性磷酸試劑盒

參考文獻(xiàn)
- Z.-L. Xia, Q.-F. Xu-Xu, C. Zheng, S.-L. You, Chiral phosphoric acid-catalyzed asymmetric dearomatization reactions. Chem. Soc. Rev. 2020, 49, 286.
- T. Varlet, G. Masson, Enamides and dienamides inphosphoric acid-catalysed enantioselective cycloadditionsfor the synthesis of chiral amines. Chem. Commun. 2021, 57, 4089.
- D. Parmar, E. Sugiono, S. Raja, M. Rueping, Completefield guide to asymmetric BINOL-phosphate derivedBrønsted acid and metal catalysis: History and classification by mode of activation; Brønsted acidity, hydrogenbonding, ion pairing, and metal phosphates. Chem. Rev. 2014, 114, 9047.
- R. Maji, S. C. Mallojjala, S. E. Wheeler, Chiral phosphoric acid catalysis: From numbers to insights. Chem. Soc. Rev. 2018, 47, 1142–1158.
- S. E. Wheeler, T. J. Seguin, Y. Guan, A. C. Doney, Noncovalent Interactions in Organocatalysis and theProspect of Computational Catalyst Design. Acc. Chem. Res. 2016, 49, 1061.
- I. O. Betinol, Y. Kuang, B. P. Mulley, J. P. Reid, Controlling Stereoselectivity with Noncovalent Interactions in Chiral Phosphoric Acid Organocatalysis. Chem. Rev. 2025, 125, 4184.
- K. Saito, H. Miyashita, T. Akiyama, Asymmetric Transfer Hydrogenation of Ketimines by Indoline as Recyclable Hydrogen Donor. Org. Lett. 2014, 16, 5312.
- T. Sakamoto, K. Mori, T. Akiyama, Chiral Phosphoric Acid Catalyzed Enantioselective Transfer Deuteration of Ketimines by Use of Benzothiazoline As a Deuterium Donor: Synthesis of Optically Active Deuterated Amines. Org. Lett. 2012, 14, 3312.
- J.-W. Lee, B. List, Deracemization of α?Aryl Hydrocoumarins via Catalytic Asymmetric Protonation of Ketene Dithioacetals. J. Am. Chem. Soc. 2012, 134, 18245.
- M. Hatano, Y. Goto, A. Izumiseki, M. Akakura, K. Ishihara, J. Am. Chem. Soc. 2015, 137, 13472.