Tributylvinyltin → HCID 58109276, compound

Participants

Reaction Steps

A mixture of (R)-3-((S)-1-(4-bromophenyl)ethyl)-6-(3-hydroxypropyl)-6-phenyl-1,3-oxazinan-2-one (3 g, 7.2 mmol), tributyl(vinyl)stannane (2.73 g, 8.64 mmol) and Pd(PPh3)4 (1 g, 0.87 mmol) in toluene (100 mL) was heated to reflux for 3 h. The reaction mixture was filtered, and the filtrate was concentrated to give the crude product, which was purified by column chromatography to afford (R)-6-(3-hydroxypropyl)-6-phenyl-3-((S)-1-(4-vinylphenyl)ethyl)-1,3-oxazinan-2-one (1.8 g, 68%). 1H NMR (CDCl3): 1.32 (m, 1H), 1.46 (m, 3H), 1.65 (m, 1H), 1.84-2.22 (m, 5H), 2.78 (m, 1H), 3.51 (m, 2H), 5.12 (m, 1H), 5.59 (m, 2H), 6.54 (m, 1H), 6.78 (m, 1H), 7.07 (m, 1H), 7.16 (m, 1H), 7.18-7.32 (m, 6H).

Provenance & Evidence