Page 5 of 9
Organic & Biomolecular Chemistry
Please do not adjust margins
Journal Name
ARTICLE
[ ]20
[ ]20
D
36.638, 21.566, 21.335; α = -25.4 (c = 1.00, CHCl3); HRMS: m/z 58.370, 55.487, 36.346, 21.537; α = +32 (c = 1.00, CHCl3); HRMS;
D
Calcd for [C23H22O3SSeNa, M + Na]+: 481.03475, Found: 481.03463.
m/z Calcd for [C23H22O4SSeNa, M + Na] : 497.02967, Found:
497.02951.
+
DOI: 10.1039/C8OB00359A
(R)-1-(4-(Tert-butyl)phenyl)-2-(phenylselanyl)-3-
tosylpropan-1-one (4h). White solid, 78% yield, m.p. 137–138
(R)-1-(3-Methoxyphenyl)-2-(phenylselanyl)-3-tosylpropan-
oC, 88% ee, determined by HPLC [Chiralcel AD-H (Hexane/i-PrOH 1-one (4l). White solid, 87% yield, m.p. 99–100 oC, 82% ee,
= 80:20, flow rate = 1.0 mL/min, wave length = 254 nm), tR = 15.069 determined by HPLC [Chiralcel OD-H (Hexane/i-PrOH = 80:20, flow
1
min (minor), tR = 17.093 min (major)]; H NMR (400 MHz, CDCl3): δ rate = 1.0 mL/min, wave length = 254 nm), tR = 11.865 min (minor),
7.749 (d, J = 8.0 Hz, 2H), 7.610 (d, J = 8.0 Hz, 2H), 7.434 (d, J = 8.4 Hz, tR = 14.183 min (major)]; 1H NMR (400 MHz, CDCl3): δ 7.617 (d, J = 8.0
2H), 7.368 (t, J = 8.0 Hz, 3H), 7.261 (t, J = 7.6 Hz, 2H), 7.155 (d, J = 8.0 Hz, 2H), 7.432 – 7.345 (m, 4H), 7.318 (d, J = 8.0 Hz, 2H), 7.290 – 7.230
Hz, 2H), 5.015 (dd, J = 10.4, 1.6 Hz, 1H), 4.191 (dd, J = 14.0, 10.8 Hz, (m, 2H), 7.172 (d, J = 8.0 Hz, 2H), 7.132 – 7.073 (m, 1H), 4.987 (dd, J
1H), 3.640 (dd, J = 14.0, 2.0 Hz, 1H), 2.348 (s, 3H), 1.355 (s, 9H); 13
C
= 10.8, 2.0 Hz, 1H), 4.180 (dd, J = 14.0, 10.8 Hz, 1H), 3.805 (s, 3H),
NMR (100 MHz, CDCl3): δ 191.524, 157.159, 144.759, 136.362, 3.661 (dd, J = 14.0, 2.0 Hz, 1H), 2.349 (s, 3H); 13C NMR (100 MHz,
135.821, 132.136, 129.712, 129.584, 129.357, 128.367, 128.213, CDCl3): δ 191.556, 159.696, 144.819, 136.360, 136.178, 135.719,
[ ]20
129.741, 129.640, 129.458, 129.352, 128.135, 125.636, 120.751,
[ ]20
125.750, 125.464, 58.336, 36.471, 35.117, 31.050, 21.551; α = -
D
15.5 (c = 1.00, CHCl3); HRMS; m/z Calcd for [C26H28O3SSeNa, M + Na]+: 119.768, 112.837, 58.282, 55.329, 36.712, 21.492; α = -10 (c =
D
523.08174, Found: 523.08188.
(R)-1-(4-Isopropylphenyl)-2-(phenylselanyl)-3-tosylpropan-
1-one (4i). White solid, 76% yield, m.p. 102–103 C, 89% ee,
1.00, CHCl3); HRMS: m/z Calcd for [C23H22O4SSeNa, M + Na]+:
497.02967, Found: 497.02985.
o
(R)-1-(2-Methoxyphenyl)-2-(phenylselanyl)-3-tosylpropan-
o
determined by HPLC [Chiralcel OD-H (Hexane/i-PrOH = 80:20, flow 1-one (4m). White solid, 66% yield, m.p. 106–108 C, 71% ee,
rate = 1.0 mL/min, wave length = 254 nm), tR = 9.754 min (minor), tR determined by HPLC [Chiralcel OD-H (Hexane/i-PrOH = 80:20, flow
= 11.302 min (major)]; 1H NMR (400 MHz, CDCl3): δ 7.742 (d, J = 8.0 rate = 1.0 mL/min, wave length = 254 nm), tR = 13.252 min (minor),
Hz, 2H), 7.607 (d, J = 8.4 Hz, 2H), 7.415 – 7.315 (m, 3H), 7.305 – 7.224 tR = 14.499 min (major)]; 1H NMR (400 MHz, CDCl3): δ 7.699 (dd, J =
(m, 4H), 7.153 (d, J = 8.0 Hz, 2H), 5.008 (dd, J = 10.6, 2.2 Hz, 1H), 4.185 7.8, 1.4 Hz, 1H), 7.665 (d, J = 8.0 Hz, 2H), 7.519 – 7.451 (m, 1H), 7.396
(dd, J = 14.2, 10.6 Hz, 1H), 3.645 (dd, J = 14.0, 2.0 Hz, 1H), 2.972 (dp, – 7.300 (m, 3H), 7.266 – 7.217 (m, 2H), 7.185 (d, J = 8.0 Hz, 2H), 6.999
J = 13.6, 7.0 Hz, 1H), 2.343 (s, 3H), 1.290 (s, 3H), 1.273 (s, 3H); 13C (t, J = 7.4 Hz, 1H), 6.945 (d, J = 8.4 Hz, 1H), 5.387 (dd, J = 10.2, 2.6 Hz,
NMR (100 MHz, CDCl3): δ 191.485, 154.889, 144.738, 136.324, 1H), 4.072 (dd, J = 14.2, 10.2 Hz, 1H), 3.871 (s, 3H), 3.559 (dd, J = 14.2,
135.767, 132.543, 129.684, 129.553, 129.321, 128.617, 128.168, 2.6 Hz, 1H), 2.354 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 191.406,
126.570, 125.716, 58.305, 36.452, 34.183, 23.598, 23.583, 21.509; 158.449, 144.635, 136.442, 136.001, 134.248, 132.012, 129.641,
[ ]20
129.330, 129.115, 128.265, 125.483, 124.674, 120.727, 111.623,
[ ]20
57.726, 55.595, 41.118, 21.547; α = +45 (c = 1.00, CHCl3); HRMS:
D
α
= -7.6 (c = 1.00, CHCl3); HRMS: m/z Calcd for [C25H26O3SSeNa, M
D
+ Na]+: 509.06608, Found: 509.06627.
(R)-2-(Phenylselanyl)-1-(p-tolyl)-3-tosylpropan-1-one (4j). m/z Calcd for [C23H22O4SSeNa, M + Na]+: 497.02967, Found:
White solid, 57% yield, m.p. 115–116 oC, 82% ee, determined by 497.02977.
HPLC [Chiralcel OD-H (Hexane/i-PrOH = 80:20, flow rate = 1.0
(R)-1-(2-Bromophenyl)-2-(phenylselanyl)-3-tosylpropan-1-
mL/min, wave length = 254 nm), tR = 10.253 min (minor), tR = 11.399 one (4n). White solid, 75% yield, m.p. 97–98 oC, 52% ee,
1
min (major)]; H NMR (400 MHz, CDCl3): δ 7.710 (d, J = 8.0 Hz, 2H), determined by HPLC [Chiralcel AD-H (Hexane/i-PrOH = 80:20, flow
7.607 (d, J = 8.0 Hz, 2H), 7.408 – 7.321 (m, 3H), 7.273 (d, J = 7.6 Hz, rate = 1.0 mL/min, wave length = 254 nm), tR = 24.183 min (major),
1
2H), 7.229 (d, J = 8.2 Hz, 2H), 7.166 (d, J = 8.4 Hz, 2H), 5.003 (dd, J = tR = 39.971 min (minor)]; H NMR (400 MHz, CDCl3): δ 7.747 (d, J =
10.6, 2.2 Hz, 1H), 4.185 (dd, J = 14.0, 10.8 Hz, 1H), 3.640 (dd, J = 14.0, 8.4 Hz, 2H), 7.661 – 7.579 (m, 2H), 7.410 (d, J = 7.6 Hz, 2H), 7.365 –
2.0 Hz, 1H), 2.426 (s, 3H), 2.353 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 7.258 (m, 5H), 7.216 (t, J = 7.4 Hz, 2H), 4.990 (dd, J = 9.6, 3.2 Hz, 1H),
191.387, 144.797, 144.252, 136.391, 135.740, 132.210, 129.738, 4.113 (dd, J = 14.4, 9.6 Hz, 1H), 3.612 (dd, J = 14.2, 3.4 Hz, 1H), 2.399
129.622, 129.356, 129.219, 128.493, 128.160, 125.618, 58.265, (s, 3H); 13C NMR (100 MHz, CDCl3): δ 193.081, 144.960, 138.268,
[ ]20
136.408, 136.084, 134.073, 132.235, 129.981, 129.882, 129.445,
129.277, 127.919, 127.113, 125.643, 121.057, 57.028, 40.723,
[ ]20
36.445, 21.659, 21.542; α = -17.8 (c = 1.00, CHCl3); HRMS: m/z
D
Calcd for [C23H22O3SSeNa, M + Na]+: 481.03475, Found: 481.03486.
(R)-1-(4-Methoxyphenyl)-2-(phenylselanyl)-3-tosylpropan-
1-one (4k). White solid, 78% yield, m.p. 95–96 oC, 85% ee, [C22H19BrO3SSeNa, M + Na]+: 544.92933, Found: 544.92954.
21.576;
α
= -25.2 (c = 1.00, CHCl3); HRMS: m/z Calcd for
D
determined by HPLC [Chiralcel AD-H (Hexane/i-PrOH = 80:20, flow
(R)-2-(Phenylselanyl)-1-(pyridin-3-yl)-3-tosylpropan-1-one
rate = 1.0 mL/min, wave length = 254 nm), tR = 30.227 min (minor), (4o). White solid, 70% yield, m.p. 97–98 oC, 68% ee, determined
tR = 35.064 min (major)]; 1H NMR (400 MHz, CDCl3): δ 7.782 (d, J = 8.8 by HPLC [Chiralcel OD-H (Hexane/i-PrOH = 80:20, flow rate = 1.0
Hz, 2H), 7.602 (d, J = 8.0 Hz, 2H), 7.416 – 7.319 (m, 3H), 7.262 (t, J = mL/min, wave length = 254 nm), tR = 19.319 min (minor), tR = 24.279
7.6 Hz, 2H), 7.164 (d, J = 8.0 Hz, 2H), 6.898 (d, J = 8.8 Hz, 2H), 4.991 min (major)]; 1H NMR (400 MHz, CDCl3): δ 9.016 (s, 1H), 8.772 (d, J =
(dd, J = 10.4, 2.0 Hz, 1H), 4.212 (dd, J = 14.0, 10.8 Hz, 1H), 3.876 (s, 4.8 Hz, 1H), 8.095 (d, J = 8.0 Hz, 1H), 7.642 (d, J = 8.4 Hz, 2H), 7.427 –
3H), 3.629 (dd, J = 14.2, 2.2 Hz, 1H), 2.352 (s, 3H);13C NMR (100 MHz, 7.318 (m, 4H), 7.272 (t, J = 7.4 Hz, 2H), 7.216 (d, J = 8.0 Hz, 2H), 4.952
CDCl3): δ 190.552, 163.720, 144.765, 136.277, 135.799, 130.716, (d, J = 10.8 Hz, 1H), 4.191 (dd, J = 13.8, 11.0 Hz, 1H), 3.694 (dd, J =
129.702, 129.543, 129.357, 128.186, 127.654, 125.890, 113.721, 10.0, 1.6 Hz, 1H), 2.375 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 190.609,
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins