(E)-3-(4-methylphenyl)prop-2-enal

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure I, a 1.38 M solution of NaOEt in ethanol (30 ml), (E)-3-(4-methylphenyl)acrylaldehyde (Compound 43, 1.1 g, 7.5 mmol) and ethyl azidoacetate (12 ml, 37.5 mmol) in EtOH (20 ml) were reacted to produce the title compound as a solid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure H, oxalyl chloride (7.1 ml, 14.2 mmol, 2 M in CH2Cl2), DMSO (1.3 ml, 18.9 mmol), (E)-3-(4-methylphenyl)prop-2-en-1-ol (Compound 41, 1.4 g, 9.5 mmol) and triethylamine (4.4 ml, 31.4 mmol) in CH2Cl2 (5 ml) were reacted to obtain the title compound as an oil. were reacted

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure I, a 1.38 M solution of NaOEt in ethanol (30 ml), (E)-3-(4-methylphenyl)acrylaldehyde (Compound 43, 1.1 g, 7.5 mmol) and ethyl azidoacetate (12 ml, 37.5 mmol) in EtOH (20 ml) were reacted to produce the title compound as a solid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure H, oxalyl chloride (7.1 ml, 14.2 mmol, 2 M in CH2Cl2), DMSO (1.3 ml, 18.9 mmol), (E)-3-(4-methylphenyl)prop-2-en-1-ol (Compound 41, 1.4 g, 9.5 mmol) and triethylamine (4.4 ml, 31.4 mmol) in CH2Cl2 (5 ml) were reacted to obtain the title compound as an oil. were reacted

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to the general procedure using (Z)-4-benzylidene-2-(2,5-difluorophenyl)-1H-imidazol-5(4H)-one and (E)-3-(p-tolyl)acrylaldehyde. The unpurified residue was purified by flash chromatography using 15% EtOAc/hexanes to afford 7 as an off-white solid (106 mg, 82%). Analytical data for 7: 1H NMR (500 MHz, CDCl3) δ 9.35 (d, J=8.1 Hz, 1H), 7.89 (ddd, J=9.2, 6.1, 3.2 Hz, 1H), 7.38-7.29 (m, 3H), 7.13 (d, J=7.7 Hz, 2H), 7.05 (ddd, J=11.4, 8.9, 4.1 Hz, 1H), 7.02-6.94 (m, 5H), 4.08 (d, J=6.8 Hz, 1H), 3.58 (ddd, J=10.2, 6.8, 4.5 Hz, 1H), 3.32 (dd, J=14.8, 4.5 Hz, 1H), 2.39 (dd, J=14.9, 10.2 Hz, 1H), 2.35 (s, 3H); 13C NMR (CDCl3, 126 MHz) δ 169.0, 159.1 (d, JCF=243.8 Hz), 155.4 (d, JCF=240.9 Hz), 148.9, 137.1, 136.34, 136.30, 134.7, 129.3, 129.2, 128.9, 128.3, 128.0, 118.4 (dd, JCF=12.8, 9.1 Hz), 117.1 (dd, JCF=25.7, 8.8 Hz), 116.5 (dd, JCF=24.7, 9.6 Hz), 114.5 (dd, JCF=26.8, 3.7 Hz), 111.1 (d, JCF=4.0 Hz), 47.4, 38.3, 32.2, 21.1; IR (film) cm−1 3029, 2923, 1768, 1618, 1529, 1482, 1463, 1452, 1351, 1240, 1172, 1118, 1102, 811, 766, 736, 700; LRMS (ESI): Mass calcd for [M+H]+ C26H21F2N2O2: 431.2. found 431.4; Enantiomeric ratio was measured by chiral phase HPLC (Chiralcel OD-H; 4% IPA/2% MeOH/hexanes; 0.7 mL/min, 280 nm), Rt1 (major)=34.4, Rt2 (minor)=43.7 min; er=99:1. Prepared The unpurified residue was purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure I, a 1.38 M solution of NaOEt in ethanol (30 ml), (E)-3-(4-methylphenyl)acrylaldehyde (Compound 43, 1.1 g, 7.5 mmol) and ethyl azidoacetate (12 ml, 37.5 mmol) in EtOH (20 ml) were reacted to produce the title compound as a solid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following General Procedure H, oxalyl chloride (7.1 ml, 14.2 mmol, 2 M in CH2Cl2), DMSO (1.3 ml, 18.9 mmol), (E)-3-(4-methylphenyl)prop-2-en-1-ol (Compound 41, 1.4 g, 9.5 mmol) and triethylamine (4.4 ml, 31.4 mmol) in CH2Cl2 (5 ml) were reacted to obtain the title compound as an oil. were reacted