X. Zhang et al. / Tetrahedron: Asymmetry 23 (2012) 468–473
473
4.4.8. 4-Hydroxy-3-methyl-4-(4-nitrophenyl)-butan-2-one
12.91 min]; 1H NMR (300 MHz, CDCl3) d: 2.10 (s, 3H), 2.67 (m,
2H), 3.55 (br s, 1H), 5.10 (dd, J = 5.0, 7.0 Hz, 1H), 7.20 (d,
J = 8.2 Hz, 2H), 7.36 (d, J = 8.2 Hz, 2H).
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 70:30,
flow rate 1.0 mL minꢁ1
, k = 254 nm; tR (anti) = 11.78 min and
11.14 min (major) and tR (syn) = 9.91 min]; 1H NMR (300 MHz,
CDCl3) d: 1.07 (t, 3H), 2.49 (q, J = 7.5, 3H), 2.86 (m, 1H), 5.63 (m,
1H), 7.51–8.92 (m, 4H).
4.4.16. 4-Hydroxyl-4-(40-bromophenyl)-butan-2-one16
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 85:15,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 11.12 min (major) and
12.91 min]; 1H NMR (300 MHz, CDCl3) d: 2.20 (s, 3H), 2.70–2.80
(m, 2H), 3.38 (br s, 1H), 5.08 (dd, J = 5.6, 7.8 Hz, 1H), 7.22 (d,
J = 8.4 Hz, 2H), 7.47 (d, J = 8.4 Hz, 2H).
4.4.9. 4-Hydroxyl-4-(40-nitrophenyl)-butan-2-one16
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 70:30,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 15.39 min and 12.08 min
(major)]; 1H NMR (300 MHz, CDCl3) d: 2.21 (s, 3H), 2.80–2.85 (m,
2H), 3.56 (br s, 1H), 5.20–5.30 (m, 1H), 7.52 (d, J = 7.0 Hz, 2H),
8.20 (d, J = 7.0 Hz, 2H).
References
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4.4.10. 4-Hydroxyl-4-(20-nitrophenyl)-butan-2-one16
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 70:30,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 12.87 min and 11.09 min
(major)]; 1H NMR (300 MHz, CDCl3) d: 2.24 (s, 3H), 2.70–2.85 (m,
2H), 3.70–3.76 (br s, 1H), 5.70 (dd, J = 9.3 Hz, 1H), 7.71 (dt, J = 1.2,
8.1 Hz, 1H), 7.44 (dt, J = 1.2, 8.1 Hz, 1H), 7.91 (dd, J = 1.2, 8.1 Hz,
1H), 7.96 (dd, J = 1.2, 8.1 Hz, 1H).
4.4.11. 4-Hydroxyl-4-(30-nitrophenyl)-butan-2-one16
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 70:30,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 11.37 min and 9.74 min
(major)]; 1H NMR (300 MHz, CDCl3) d: 2.23 (s, 3H), 2.82 (m, 2H),
3.50 (br s, 1H), 5.15–5.27 (m, 1H), 7.53 (t, J = 7.5 Hz, 1H), 7.71
(d, J = 7.5 Hz, 1H), 8.13 (d, J = 8.6 Hz, 1H), 8.24 (s, 1H).
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Enders, D. Nat. Chem. 2010, 2, 167; (d) Mason, B. P.; Bogdan, A. R.; Goswami, A.;
McQuade, D. T. Org. Lett. 2007, 9, 3449; (e) Thierry, B.; Plaquevent, J. C.; Cahard,
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Chem. 2010, 8, 269.
4.4.12. 4-(20,40-Dinitrophenyl)-4-hydroxylbutan-2-one
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 70:30,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 16.77 min (major) and
11.29 min]; 1H NMR (300 MHz, CDCl3) d: 2.13 (s, 3H), 2.79–3.06
(m, 2H), 3.65 (br s, 1H), 4.73 (dd, J = 9.3 Hz, 1H), 7.88 (dt, J = 1.2,
8.1 Hz, 1H), 8.53 (dd, J = 1.2, 8.1 Hz, 1H), 8.84 (dd, J = 1.2 Hz, 1H).
4.4.13. 4-Hydroxyl-4-(40-cyanophenyl)-butan-2-one16
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 85:15,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 17.68 min and 10.70 min
(major)]; 1H NMR (300 MHz, CDCl3) d: 2.21 (s, 3H), 2.82 (m, 2H),
3.32 (br s, 1H), 5.20 (m, 1H), 7.47 (d, J = 8.1 Hz, 2H), 7.64 (d,
J = 8.1 Hz, 2H).
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Synthesis 2009, 22, 3744.
4.4.14. 4-Hydroxyl-4-(40-fluorophenyl)-butan-2-one16
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 85:15,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 11.12 min (major) and
12.91 min]; 1H NMR (300 MHz, CDCl3) d: 2.23 (s, 3H), 2.87
(m, 2H), 3.35 (br s, 1H), 5.16 (dd, J = 4.6, 6.6 Hz, 1H), 7.09
(d, J = 8.0 Hz, 2H), 7.38 (d, J = 8.0 Hz, 2H).
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11, 1450.
4.4.15. 4-Hydroxyl-4-(40-chlorophenyl)-butan-2-one16
[Daicel Chiralpak AS-H column, n-hexane/isopropanol = 85:15,
flow rate 1.0 mL minꢁ1, k = 254 nm; tR = 11.12 min (major) and