Synthesis and chiral recognition ability of O-ethyl (2-naphthyl)phosphonothioic acid |
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| Affiliation: | 1. Department of Endocrinology and Metabolism, Shanghai Jiao Tong University Affiliated Sixth People’s Hospital, Shanghai Clinical Center for Diabetes, Shanghai Diabetes Institute, Shanghai Key Laboratory of Diabetes Mellitus, Shanghai Key Clinical Center for Metabolic Disease, 600 Yishan Road, Shanghai, 200233, China;2. Department of ophthalmology, Shanghai Jiao Tong University Affiliated Sixth People’s Hospital, 600 Yishan Road, Shanghai 200233, China;3. Department of VIP, Shanghai Jiao Tong University Affiliated Sixth People’s Hospital, 600 Yishan Road, Shanghai 200233, China |
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| Abstract: | Enantiopure O-ethyl (2-naphthyl)phosphonothioic acid 1 was designed on the model of O-ethyl phenylphosphonothioic acid, based on the fact that the chiral recognition abilities of enantiopure mandelic acid and cis-1-aminoindan-2-ol were improved upon by replacing their phenyl/phenylene groups with naphthyl/naphthylene groups, respectively. Enantiopure 1 was easily obtained by the enantioseparation of racemic 1, which was easily synthesized from commercially available 2-bromonaphthalene and diethoxyphosphonothioic chloride, with enantiopure 1-phenylethylamine. Enantiopure 1 showed an excellent chiral recognition ability for several 1-arylethylamine derivatives during the diastereomeric salt formation. The effect of the enlarged aromatic part of 1 is discussed on the basis of X-ray crystallographic analyses. |
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