Reaction Steps
A 5 mL microwave vial was charged with (2S,3S,4R,5S,6R)-2-(3-(4-chlorobenzyl)-4-methylphenyl)-6-(methylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate (7, 208 mg, 0.40 mmol), but-3-enenitrile (0.10 mL, 1.2 mmol), Pd2 dba3 (37 mg, 0.040 mmol), tri(tert-butyl)phosphonium tetrafluoroborate (46 mg, 0.16 mmol), dicyclohexylmethylamine (0.25 mL, 1.2 mmol), and 2 mL of N-methylpyrrolidinone. The reaction was heated in the microwave at 160° C. for 20 min. The reaction was filtered over Celite with excess EtOAc. The organic layer was washed with H2O, saturated aqueous NaHSO4, and brine. It was dried with MgSO4 and concentrated in vacuo. Flash chromatography (gradient 10-80% EtOAc/hexanes) provided the Heck adduct 28 (140 mg, 64% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.24-7.31 (m, 2 H), 7.11-7.20 (m, 2H), 7.02-7.09 (m, 3 H), 6.70 (dt, J=15.9, 1.6 Hz, 1 H), 6.01 (dt, J=15.8, 5.7 Hz, 1 H), 5.33 (t, J=9.3 Hz, 1 H), 5.21 (t, J=9.7 Hz, 1 H), 5.12 (t, J=9.6 Hz, 1 H), 4.52 (d, J=9.9 Hz, 1 H), 4.39 (d, J=9.9 Hz, 1 H), 3.95 (d, J=3.5 Hz, 2 H), 3.28 (dd, J=5.8, 1.8 Hz, 2 H), 2.20 (s, 3 H), 2.16 (s, 3 H), 2.09 (s, 3 H), 2.01 (s, 3 H), 1.75 (s, 3 H). MS (ES+) [M+NH4]+=567.
