GENC
3
1
(R)‐10‐(1‐(4‐Chlorophenyl)‐2‐nitroethyl)anthracen‐
9(10H)‐one 7c33
1,661; H NMR (400 MHz, CDCl3): δ = 4.01 to 4.06 (m,
1H), 4.56 to 4.62 (m, 2H), 4.89 (dd, J = 13.3, 8.8 Hz,
1H), 5.99 (d, J = 7.3 Hz, 1H), 6.17 (s, 1H), 6.86 (t,
J = 7.9 Hz, 1H), 7.32 (d, J = 9.1 Hz, 1H), 7.42 to 7.59
(m, 4H), 7.65 to 7.71 (m, 2H), 8.05 (d, J = 7.6 Hz, 1H),
8.15 (d, J = 7.7 Hz, 1H); 13C NMR (100 MHz, CDCl3):
δ = 45.9, 53.0, 76.1, 121.9, 126.6, 127.2, 127.6, 128.3,
128.4, 128.5, 128.7, 129.6, 131.6, 131.9, 132.7, 133.0,
133.5, 134.6, 135.7, 139.0, 141.6, 183.0; HPLC (AS‐H col-
umn, hexane–IPA = 80:20, l = 254 nm, 1.0 mL/min flux,
tR = 14.71 minutes (major); 17.55 minutes (minor).
White solid, yield 92%; 80% ee, α2D5 = +23.2 (c 0.5, CHCl3);
Mp 168°C to 171°C; IR (cm−1): 929, 1,321, 1,549, 1,600,
1
1,659; H NMR (400 MHz, CDCl3): δ = 4.01 to 4.04 (m,
1H), 4.49 (d, J = 3.4 Hz, 1H), 4.60 (dd, J = 13.3, 7.6 Hz,
1H), 4.87 (dd, J = 13.3, 8.5 Hz, 1H), 5.99 (d, J = 8.5 Hz,
2H), 6.92 (d, J = 8.5 Hz, 2H), 7.40 to 7.55 (m, 4H), 7.61
to 7.67 (m, 2H), 8.03 (d, J = 7.9 Hz, 1H), 8.09 (d,
J = 7.6 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ = 45.8,
52.5, 76.4, 126.8, 127.0, 127.2, 127.6, 127.9, 128.1 128.2,
128.4, 130.0, 131.9, 132.2, 132.9, 133.1, 134.0, 134.5,
138.9, 141.7, 182.9; HPLC (AS‐H column, hexane–IPA =-
90:10, l = 254 nm, 1.0 mL/min flux, tR = 22.21 minutes
(major); 26.44 minutes (minor).
(R)‐10‐(1‐(2‐Methoxyphenyl)‐2‐nitroethyl)anthracen‐
9(10H)‐one 7g33
White solid, yield 88%; 96% ee, α2D5 = −8.1 (c 0.8, CHCl3);
Mp 129°C to 131°C; IR (cm−1): 929, 13,20, 1,509, 1,555,
1
(R)‐10‐(1‐(4‐Methoxyphenyl)‐2‐nitroethyl)anthracen‐
9(10H)‐one 7d33
1,600, 1,661; H NMR (400 MHz, CDCl3): δ = 3.19 (s,
1H), 4.39 to 4.43 (m, 1H), 4.69 (d, J = 3.9 Hz, 1H), 4.79
(dd, J = 13.1, 10.1 Hz, 1H), 5.09 (dd, J = 13.4, 5.9 Hz,
1H), 6.03 (d, J = 6.5 Hz, 1H), 6.50 (t, J = 7.4 Hz, 1H),
6.70 (d, J = 8.0 Hz, 1H), 7.10 (t, J = 7.3 Hz, 1H), 7.39 to
7.50 (m, 4H), 7.59 to 7.62 (t, J = 7.4 Hz, 2H), 7.82 (d,
J = 7.4 Hz, 1H), 7.89 (m, J = 7.9 Hz, 1H); 13C NMR
(100 MHz, CDCl3): δ = 44.9, 45.0, 54.8, 76.7, 109.9,
120.4, 121.3, 124.6, 125.8, 126.2, 127.5, 128.0, 128.4,
129.0, 129.4, 131.9, 132.9, 141.0, 142.6, 156.9, 183.0; HPLC
(AS‐H column, hexane–IPA = 80:20, l = 254 nm, 1.0 mL/
min flux, tR = 10.85 minutes (major); 13.80 minutes
(minor).
White solid, yield 94%; 90% ee, α2D5 = +18.3 (c 0.7, CHCl3);
Mp 119°C to 121°C; IR (cm−1): 929, 1,312, 1,511, 1,548,
1
1,599, 1,671; H NMR (400 MHz, CDCl3): δ = 3.71 (s,
3H), 3.99 to 4.01 (m, 1H), 4.49 (d, J = 3.8 Hz, 1H), 4.57
(dd, J = 13.3, 7.4 Hz, 1H), 4.82 (dd, J = 13.3, 9.1 Hz, 1H),
6.00 (d, J = 8.8 Hz, 2H), 650 (d, J = 8.8 Hz, 2H), 7.40 to
7.54 (m, 4H), 7.60 to 7.67 (m, 2H), 8.02 (d, J = 7.9 Hz,
1H), 8.10 (d, J = 7.3 Hz, 1H); 13C NMR (100 MHz, CDCl3):
δ = 45.9, 52.4, 54.9, 76.9, 113.2, 125.0, 127.1, 127.5, 127.8,
128.0, 128.2, 128.3, 129.4, 132.6, 132.8, 133.9, 134.8, 139.0,
141.9, 160.0, 182.9; HPLC (OD‐H column, hexane–IPA =-
80:20, l = 254 nm, 1.0 mL/min flux, tR = 26.40 minutes
(major); 19.72 minutes (minor).
(R)‐10‐(2‐nitro‐1‐(2‐Nitrophenyl)ethyl)anthracen‐
9(10H)‐one 7h33
White solid, yield 90%; 90% ee, α2D5 = −5.2 (c 0.3, CHCl3);
Mp 69°C to 72°C; IR (cm−1): 936, 1,313, 1,529, 1,551,
(R)‐10‐(2‐nitro‐1‐(p‐tolyl)ethyl)anthracen‐9(10H)‐one
7e33
1
White solid, yield 96%; 97% ee, α2D5 = +24.9 (c 0.6, CHCl3);
1,604, 1,670; H NMR (400 MHz, CDCl3): δ = 4.69 to
Mp 156°C to 158°C; IR (cm−1): 929, 1,315, 1,548, 1,600,
4.74 (m, 1H) 4.83 (d, J = 5.2 Hz, 1H), 5.09 (dd, J = 13.6,
10.3 Hz, 1H), 5.30 (dd, J = 13.9, 5.5 Hz, 1H), 6.69 to
6.72 (m, 1H), 7.29 to 7.38 (m, 3H), 7.48 to 7.62 (m, 6H),
7.90 (dd, J = 13.9, 7.6 Hz, 2H); 13C NMR (100 MHz,
CDCl3): δ = 44.9, 45.5, 76.8, 123.9, 125.8, 126.1, 127.6,
127.8, 128,2, 128.9, 129.1, 129.2, 129.5, 131.9, 132.0,
132.5, 132.9, 134.0, 140.0, 140.9, 150.0, 183.1; HPLC
(OD‐H column, hexane–IPA = 70:30, l = 254 nm,
1
1,659; H NMR (400 MHz, CDCl3): δ = 2.09 (s, 3H), 4.00
to 4.04 (m, 1H), 4.49 (d, J = 3.5 Hz, 1H), 4.54 (dd,
J = 13.1, 7.1 Hz, 1H), 4.82 (dd, J = 13.1, 8.9 Hz, 1H), 5.99
(d, J = 8.0 Hz, 2H), 6.74 (d, J = 7.7 Hz, 2H), 7.35 to 7.45
(m, 2H), 7.49 (d, J = 7.4 Hz, 2H), 7.56 to 7.61 (m, 2H),
8.03 (d, J = 7.7 Hz, 1H), 8.10 (d, J = 7.3 Hz, 1H); 13C
NMR (100 MHz, CDCl3): δ = 20.9, 45.9, 53.1, 75.8, 126.4,
126.9, 127.4, 127.9, 128.3, 128.5, 128.6, 129.9, 132.4, 132.8,
133.4, 134.3, 138.1, 139.3, 142.0, 182.9; HPLC (AS‐H col-
umn, hexane–IPA = 90:10, l = 254 nm, 1.0 mL/min flux,
tR = 15.91 minutes (major); 18.04 minutes (minor).
1.0 mL/min flux, tR
17.94 minutes (minor).
=
15.17 minutes (major);
(R)‐10‐(1‐(2‐Bromophenyl)‐2‐nitroethyl)anthracen‐
9(10H)‐one 7i33
(R)‐10‐(1‐(3‐Bromophenyl)‐2‐nitroethyl)anthracen‐
9(10H)‐one 7f33
White solid, yield 95%; 96% ee, α2D5 = +31.5 (c 0.6, CHCl3);
Mp 115°C to 117°C; IR (cm−1): 934, 1,313, 1,549, 1,600,
White solid, yield 93%; 85% ee, α2D5 = +6.9 (c 0.7, CHCl3);
Mp 63°C to 65°C; IR (cm−1): 938, 1,320, 1,555, 1,601,
1
1,659; H NMR (400 MHz, CDCl3): δ = 4.00 to 4.03 (m,
1H), 4.81 (d, J = 5.4 Hz, 1H), 4.89 to 5.01 (m, 1H), 5.12