Guivisdalsky, Pedro N. published the artcileGlycidyl derivatives as chiral C3 synthons. Ring opening catalyzed by boron trifluoride etherate, Quality Control of 115314-17-5, the publication is Journal of the American Chemical Society (1989), 111(8), 3077-9, database is CAplus.
The BF3.OEt2 mediated regio- and stereoselective opening reactions of (R)- and (S)-glycidyl arenesulfonates I (R = 4-MeC6H5SO2, 3-O2NC6H4SO2) and tert-butyldiphenylsilyl ether I (R = Me3CPh2Si) with R1XH [R1 = PhCH2, Me(CH)15, oleyl, petroselinyl, X = O; R1 = Ph, X = S] in CH2Cl2 or CHCl3 is reported. BF3.Et2 was a more effective catalyst than other Lewis acids used previously for opening of glycidol, giving rise to (+)- and (-)-ROCH2CH(OH)CH2XR1 (R, R1, X = same as above) in good yield and high enantiomeric excess. Glycidyl arenesulfonates underwent attack exclusively at C(3), whereas the silyl ethers gave products resulting from C(3):C(2) attack in a ratio of 9:1. The BF3.Et2O catalyzed opening of glycidyl derivatives is a more convenient method for preparing suitably protected vic-diols than the previously described Ti-mediated opening the the parent glycidol.
Journal of the American Chemical Society published new progress about 115314-17-5. 115314-17-5 belongs to esters-buliding-blocks, auxiliary class Epoxides,Chiral,Nitro Compound,Sulfonate,Benzene, name is (R)-Oxiran-2-ylmethyl 3-nitrobenzenesulfonate, and the molecular formula is C9H9NO6S, Quality Control of 115314-17-5.
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