Abstract:
By the spontaneous resolution of racemic compound 1,8-bis(dimethylamino)-2-(α-hydroxy-α-phenylethyl)naphthalene (±)-1, enantiomer (–)-1 was obtained; its treatment with C5H5N·HBr resulted in the formation of proton sponge (–)-2; the absolute configurations of (R)-(–)-2 and, as a consequence, (R)-(–)-1 were determined by XRD analysis.
Document Type:
Article
Language: English
Citation:
R. G. Kostyanovsky, A. F. Pozharskii, Yu. V. Nelyubina, K. A. Lyssenko, G. K. Kadorkina, A. V. Degtyarev, O. G. Nabiev, I. I. Chervin, “Absolute configuration of a chiral proton sponge”, Mendeleev Commun., 18:2 (2008), 86–87
Linking options:
https://www.mathnet.ru/eng/mendc3257
https://www.mathnet.ru/eng/mendc/v18/i2/p86
This publication is cited in the following 3 articles:
Huiwen Shi, Xiufen Jiang, Liudan Cao, Xing Peng, Qingyun Tan, Xifeng Teng, Qiong Gu, Lin He, “Chemical constituents of Ajuga forrestii and their anti-ferroptosis activity”, Fitoterapia, 166 (2023), 105461
Lee Belding, Peter Stoyanov, Travis Dudding, “Synthesis, Theoretical Analysis, and Experimental pKa Determination of a Fluorescent, Nonsymmetric, In–Out Proton Sponge”, J. Org. Chem., 81:1 (2016), 6
Jean-Paul Mazaleyrat, Karen Wright, “Binaphthyl substituted 1,8-bis(dimethylamino)naphthalenes, the first chiral, atropisomeric, proton sponges”, Tetrahedron Letters, 49:29-30 (2008), 4537
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