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6.73 (d, 1H, J = J = 3.60 Hz, C(3)H thiophene ring), 7.16–7.32(m, 5H,
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71.45, 76.15, 105.97, 108.06, 122.13, 127.10, 128.12, 129.45,
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5.09; O, 5.81; S, 11.64. Found: C, 69.76; H, 7.68; N, 5.10; O, 5.80;
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4.2.4. (1S,2R)-2-((5-Ethylthiophen-2-yl)methyleneamino)-1-
phenylpropan-1-ol (1S,2R)-5b
Brown oil, 78% yield; Rf: 0.16 (EtOAc:hexane, 1:1); IR (KBr) (
m
max/cmÀ1): 3345, 2978, 2858, 2742, 2650, 1640, 1418, 1370,
1336, 1245, 1185, 1138, 1079, 998, 727, 708; 1H NMR: (CDCl3,
400 MHz)
d 0.81 (d, 3H, J = 6.4, NHCHCH3), 2.54 (q, 2H,
J = 7.60 Hz, CH2CH3), 2.89–2.952 (m, 1H, NHCHCH3), 4.86 (d, 1H,
J = 3.60 Hz, CHOH), 6.61 (d, 1H, J = 3.60 Hz, C(4)H,, thiophene ring),
6.82 (d, 1H, J = 3.60 Hz, C(3)H, thiophene), 7.16–7.30 (m, 5H, ArH),
8.12 (s, 1H, CH@N). 13C NMR (CDCl3, 100 MHz) d 13.68, 14.60,
44.10, 57.21, 78.15, 105.97, 108.06, 126.07–128.90, 141.26,
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Compound VO(acac)2 (2.7 mg, 0.01 mmol) and chiral ligand
(0.015 mmol) were dissolved in CH2Cl2 (1 mL). The mixture was
stirred for 30 min under an argon atmosphere at 0 °C. A solution
of sulfide (1.0 mmol) in CH2Cl2 (1 mL) was then added, followed
by dropwise addition (ca. 30 min) of aqueous H2O2 (30%, 1.2 mmol)
at 0 °C. The reaction progress was monitored by TLC analysis. After
the mixture was stirred at 0 °C for 10 h, the resulting solution was
extracted with CH2Cl2. The organic layer was washed with brine
and dried over Na2SO4. Filtration and evaporation gave a residue
which was purified by flash chromatography on silica gel with
petroleum ether/ethyl acetate (3:2, v/v) and ethyl acetate as elu-
ents. The pure sulfoxide was obtained after removal of the solvent
by rotary evaporation. The adducts were fully characterized by
comparison of their spectroscopic data with those reported in the
literature. The enantiomeric purity of the product was determined
by HPLC analysis. The absolute configuration of the products was
assigned by comparison to the literature data.27,29b,37
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