Stereochemistry of chiral pentacoordinate spirophosphoranes correlated with solid-state circular dichroism and 1H NMR spectroscopy |
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Authors: | Jian-Bo Hou Guo Tang Jian-Nan Guo Yan Liu Hui Zhang Yu-Fen Zhao |
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Institution: | 1. Department of Chemistry, College of Chemistry and Chemical Engineering, and The Key Laboratory for Chemical Biology of Fujian Province, Xiamen University, Xiamen 361005, PR China;2. Department of Pharmaceutical Science, Medical College, Xiamen University, Xiamen 361005, PR China;3. The Key Laboratory for Bioorganic Phosphorus Chemistry, Ministry of Education, Department of Chemistry, School of Life Science and Engineering, Tsinghua University, Beijing 100084, PR China |
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Abstract: | Two sets of diastereomers of pentacoordinate spirophosphoranes separately derived from l-valine (or d-valine) and l-leucine (or d-leucine) were synthesized, isolated, and structurally characterized both in the solid state (X-ray crystallography and solid-state CD spectroscopy) and in the solution (1H NMR). The Λ and Δ absolute configurations of a pair of enantiomers 3a and 4a with distorted trigonal bipyramids (TBPs) geometry are directly determined by X-ray diffraction analysis, respectively. The chiral-at-phosphorus features of the related diastereomers were correlated with their solid-state CD and 1H NMR spectra. |
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