|
|
Structural Characterization of ((S)-2΄-Hydroxy-1,1΄- binaphthalen-2-yl)-(SP)-vinylphosphonate Synthesized by the Chiral Induced Diastereoselective Reaction |
JIANG Jie;LIU Feng-Jiao;ZHU Zhong-Xiang;WU Ming-Shu |
(Key Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, China) |
|
|
Abstract Ethyl((S)-2΄-hydroxy-1,1΄-binaphthalen-2-yl)-(SP)-vinylphosphonate (SBINOL-SP) was synthesized by diastereoselective reaction and characterized by means of NMR spectroscopy, H RMS and X-ray diffraction. The single crystal belongs to the monoclinic system, space group P21/c with a = 7.4983(13), b = 12.065(2), c = 21.805(4) Å, β = 90.094(6)°, Mr = 404.38, V = 1972.6(6) Å3, Z = 4, Dc = 1.362 g/cm3, F(000) = 848, μ = 0.168 mm-1, R = 0.0280 and wR = 0.0743. The title compound shows good activities against E. coli, S. albus, B. subtilis and M. tetragenus.
|
Received: 30 September 2016
Published: 10 July 2017
|
Corresponding Authors:
wmsh@hainnu.edu.cn
E-mail: wmsh@hainnu.edu.cn
|
|
|
|
REFERENCES
(1)Dubrovina, N. V.; Börner, A. Enantioselective catalysis with chiral phosphine oxide preligands. Angewandte Chemie International Edition 2004, 43, 5883.
(2) Pietrusiewicz, K. M.; Zablocka, M. Preparation of scalemic P-chiral phosphines and their derivatives. Corros. Rev. 1994, 94, 1375.
(3) Korpiun, O.; Mislow, K. New route to the preparation and configurational correlation of optically active phosphine oxides. J. Am. Chem. Soc. 1967, 89, 4784.
(4) Han, L. B.; Zhao, C. Q. Stereospecific addition of H−P bond to alkenes: a simple method for the preparation of (RP)-phenylphosphinates. J. Org. Chem. 2005, 70, 10121.
(5) Han, L. B.; Zhao, C. Q.; Onozawa, S. Y.; Goto, M.; Tanaka, M. Retention of configuration on the oxidative addition of P−H bond to platinum (0) complexes: the first straightforward synthesis of enantiomerically pure P-chiral alkenylphosphinates via palladium-catalyzed stereospecific hydrophosphinylation of alkynes. J. Am. Chem. Soc. 2002, 124, 3842.
(6) Berger, O.; Montchamp, J.L. A general strategy for the synthesis of P-stereogenic compounds. Angewandte Chemie International Edition 2013, 52, 11377.
(7) Li, G. Z.; Lui F. L.; Wu, M. S. BINOLs modified at the 3,3′-positions: chemists' preferred choice in asymmetric catalysis. Arkivoc 2015, 140.
(8) Fourgeaud, P.; Midrier, C.; Vors, J. P.; Volle, J. N.; Pirat, J. L.; Virieux, D. Oxaphospholene and oxaphosphinene heterocycles via RCM using unsymmetrical phosphonates or functional phosphinates. Tetrahedron 2010, 66, 758.
(9) Maffei, M.; Buono, G. A two step synthesis of 2-oxo-2-vinyl 1,3,2-dioxaphospholanes and -dioxaphosphorinanes. Tetrahedron 2003, 59, 8821.
(10) Tsotinis, A.; Gerasimopoulou, M.; Vlachou, M.; Moreau, D.; Roussakis, C. C5,C6-Disubstituted 1H-indole-2-carboxamides: synthesis and cytotoxic activity in the human non-small lung cancer cell line NSCLC-N16-L16. Lett. Drug Des. Discov. 2006, 3, 14. |
|
|
|