2-Benzyl-1,3-oxazolidine → HCID 178527704, compound

Participants

Reaction Steps

To a clear solution of the 2-(2-hydroxyphenyl)-(4S)-isopropyloxazolidine (3.7 g, 18.0 mmol) in benzene (150 mL), at reflux, was added bis(triphenylphosphine) oxorhenium(V) trichloride (1.5 g, 1.80 mmol). The resulting green solution was refluxed for 2 h, cooled to room temperature and concentrated to approximately 50 mL. The green precipitate was collected and washed with diethyl ether (3×50 mL), to afford the chiral rhenium complex (1.10 g, 83%) as a green solid. 1H-NMR (CD2Cl2): δ 7.60−7.37 (m, 19H), 7.12 (ddq, J=8.2, 7.1 and 1.8 Hz, 1H), 6.91 (td, J=7.1 and 1.8 Hz, 1H), 6.63 (dd, J=8.2 and 0.8 Hz), 4.48 (dd, J=9.8 and 4.3 Hz, 1H), 3.96 (t, J=9.8 Hz, 1H), 3.57 (ddd, J=9.8, 4.0 and 2.8 Hz, 1H), 2.92 (m, 1H), 1.00 (d, J=6.6 Hz, 3H), 0.82 (d, J=7.1 Hz, 3H). 31P-NMR (CD2Cl2): −18.5. An analogous procedure was carried out to synthesize the benzyloxazolidine analogue using 2-(2-hydroxyphenyl)-(4S)-benzyloxazolidine as a starting material.

Provenance & Evidence