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The reported chemical shift is 27.2 ppm upfield from trimethyl borate in benzene; our chemical shift value is referenced to boron trifluoride etherate in deuterochloroform
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A value of δ 17.6 ppm is reported for diborane in chloroform by Kanth, J. V. B.; Brown, H. C. Tetrahedron Lett. 2000, 41, 9361.
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Reference 24a describes several reactions of alkenes in the presence of chiral tertiary N-phenylamines. By far the highest enantioselectivities were reported with 2,3-dihydrofuran (0.7 g scale, benzene solution) in the presence of a 1:1 ratio of in situ generated amine boranes i (11.6 ± 2.3% ee for 3-hydroxytetrahydrofuran) or ii (19.2 ± 2.4% ee for 3-hydroxytetrahydrofuran) using a workup consisting of standard base/peroxide oxidative cleavage followed by distillation from the crude product mixture, Chemical Equation Presented) chromatography, redistillation, and ee assay based on optical rotation. In two attempts to repeat the reaction using i (0.107 and 0.056 g scale, we opted not to perform the distillations due to the smaller quantities. The usual uncertainties involving optical rotation were another consideration. Starting with i found αD +19.2, c 3.2, CHCl3; reported αD
-
N2-like displacement of amine by alkene as proposed in ref 24, or to non-covalent interactions involving the chiral amine in the transition state. Except for the experiments using i or ii with 2,3-dihydrofuran in ref 24a, the other examples described in ref 24a, b report ee values in the range of 1-5% ee based on optical rotation.
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