8
A. Bhalla et al. / Tetrahedron: Asymmetry xxx (2017) xxx–xxx
(10H, m, ArH), 6.21 (1H, d, J = 5.3 Hz, C3-H), 5.18 (1H, q, J = 7.4 Hz,
CHCH3), 4.97 (1H, d, J = 5.3 Hz, C4-H), 1.95 (3H, d, J = 7.1 Hz,
CHCH3), 1.65 (3H, s, CH3COO); 13C NMR (75 MHz, CDCl3, Both iso-
mers) d 169.7, 169.6, 164.5, 164.3, 140.8, 139.7, 137.0, 136.6, 136.1,
136.0, 129.1, 129.1, 129.0, 128.9, 128.7, 128.7, 128.3, 128.2, 127.5,
127.3, 126.9, 123.7, 122.5, 76.5, 76.5, 60.1, 59.6, 53.5, 52.6, 20.6,
19.7, 19.1; Anal. Calcd. for C20H19NO4: C, 71.20; H, 5.68; N, 4.15.
Found: C, 71.15; H, 5.64; N, 4.11.
4.3.9. (10S, 3R, 4S)- and (10S, 3S, 4R)-1-(10-Phenylpropyl)-3-
acetoxy-4-phenylazetidin-2-one 2i/20i
IR (ATR) m
max 1751, 1602, 1527 cmꢀ1; 1H NMR (300 MHz, CDCl3,
Major isomer) d 7.06–7.27 (10H, m, ArH), 5.56 (1H, d, J = 4.5 Hz,
C3-H), 4.56–4.58 (1H, m, CHCH2), 4.52 (1H, d, J = 4.8 Hz, C4-H),
1.78–1.88 (1H, m, CHCH2), 1.62–1.69 (1H, m, CHCH2), 1.59 (3H, s,
CH3COO), 0.78 (3H, t, J = 7.2 Hz, CH2CH3); 1H NMR (300 MHz,
CDCl3, Minor isomer) d 7.06–7.27 (m, 10H, ArH), 5.61 (1H, d,
J = 4.5 Hz, C3-H), 4.56–4.58 (1H, m, C4-H), 3.97 (1H, t, J = 8.1 Hz,
CHCH2), 2.42–2.47 (1H, m, CHCH2), 2.00–2.04 (1H, m, CHCH2),
1.57 (3H, s, CH3COO), 0.92 (3H, t, J = 7.2 Hz, CH2CH3), 13C NMR
(75 MHz, CDCl3, Both isomers) d 169.1, 169.0, 164.8, 164.6, 139.2,
137.7, 133.9, 133.7, 132.7, 128.7, 128.6, 128.5, 128.4, 128.1,
128.0, 127.9, 127.9, 127.8, 127.2, 76.4, 76.2, 61.6, 61.6, 60.4, 60.1,
26.7, 26.3, 19.8, 19.8, 11.7, 11.1; Anal. Calcd. for C20H21NO3: C,
74.28; H, 6.55; N, 4.33. Found: C, 74.22; H, 6.50; N, 4.29.
4.3.6. (10R,3R,4S)- and (10R,3S,4R)-1-(10-Phenylethyl)-3-acetoxy-
4-phenylazetidin-2-one 2f/20f
IR (ATR) m
max 1753, 1602 cmꢀ1 1H NMR (400 MHz, CDCl3, Major
isomer) d 7.15–7.34 (10H, m, ArH), 5.65 (1H, d, J = 4.7 Hz, C3-H),
5.07 (1H, q, J = 7.1 Hz, CHCH3), 4.66 (1H, d, J = 4.7 Hz, C4-H), 1.66
(3H, s, CH3COO), 1.38 (3H, d, J = 7.2 Hz, CHCH3); 1H NMR
(400 MHz, CDCl3, Minor isomer) d 7.15–7.34 (10H, m, ArH), 5.70
(1H, d, J = 4.6 Hz, C3-H), 4.70 (1H, d, J = 4.7 Hz, C4-H), 4.41 (1H, q,
J = 7.3 Hz, CHCH3), 1.84 (3H, d, J = 7.2 Hz, CHCH3), 1.64 (3H, s,
CH3COO), 13C NMR (100 MHz, CDCl3, Both isomers) d 169.1,
169.0, 164.7, 140.3, 139.1, 134.0, 132.7, 128.8, 128.7, 128.6,
128.5, 128.4, 128.1, 128.0, 127.9, 127.1, 126.7, 76.5, 76.3, 60.9,
60.7, 54.6, 52.4, 19.8, 19.7, 19.0; Anal. Calcd. for C19H19NO3: C,
73.77; H, 6.19; N, 4.53. Found: C, 73.70; H, 6.20; N, 4.55.
4.3.10. (10S,3R,4S)- and (10S,3S,4R)-1-(10-Phenylpropyl)-3-
acetoxy-4-styrylazetidin-2-one 2j/20j
White needles; m.p.: 132–133 °C; IR (ATR) mmax 1752, 1650,
1601 cmꢀ1
;
1H NMR (300 MHz, CDCl3, Major isomer, Pure) d
7.18–7.30 (10H, m, ArH), 6.45 (1H, d, J = 15.9 Hz, CH@CHPh), 5.91
(1H, dd, J = 15.6, 9.0 Hz, CH@CHPh), 5.59 (1H, d, J = 4.8 Hz, C3-H),
4.51 (1H, t, J = 7.5 Hz, CHCH2), 4.17 (1H, dd, J = 8.7, 4.8 Hz, C4-H),
1.98–2.10 (1H, m, CH2CH3), 1.96 (3H, s, CH3COO), 1.83–1.93 (1H,
m, CH2CH3), 0.91 (3H, t, J = 7.2 Hz, CH2CH3); 1H NMR (300 MHz,
CDCl3, Minor isomer) d 7.15–7.48 (10H, m, ArH), 6.40 (1H, d,
J = 16.2 Hz, CH@CHPh), 5.73 (1H, dd, J = 16.2, 8.4 Hz, CH@CHPh),
5.58 (1H, d, J = 4.8 Hz, C3-H), 4.12–4.17 (1H, t, J = 8.1 Hz, CHCH2),
4.12–4.17 (1H, dd, J = 8.7, 4.8 Hz, C4-H), 1.98–2.08 (1H, m, CH2-
CH3), 1.90–1.92 (1H, m, CH2CH3), 1.95 (3H, s, CH3COO), 0.82 (3H,
t, J = 6.9 Hz, CH2CH3); Anal. Calcd. for C22H23NO3: C, 75.62; H,
6.63; N, 4.01. Found: C, 75.60; H, 6.59; N, 3.99.
4.3.7. (10R, 3R, 4S)- and (10R, 3S, 4R)-1-(10-Naphthylethyl)-3-
acetoxy-4-phenylazetidin-2-one 2g/20g
White solid; IR (ATR) mmax 1748, 1711, 1599 cmꢀ1 1H NMR
;
(300 MHz, CDCl3, Major isomer) d 6.86–8.01 (12H, m, ArH), 5.87
(1H, q, J = 6.9 Hz, CHCH3), 5.42 (1H, d, J = 4.8 Hz, C3-H), 4.01 (1H,
d, J = 4.8 Hz, C4-H), 1.58 (3H, s, CH3COO), 1.48 (3H, d, J = 7.2 Hz,
CHCH3); 1H NMR (300 MHz, CDCl3, Minor isomer) d 6.85–8.01
(12H, m, ArH), 5.66 (1H, d, J = 4.5 Hz, C3-H), 5.29 (1H, q,
J = 6.9 Hz, CHCH3), 4.66 (1H, d, J = 4.8 Hz, C4-H), 1.90 (3H, d,
J = 7.2 Hz, CHCH3), 1.54 (3H, s, CH3COO); 13C NMR (75 MHz, CDCl3,
Both isomers) d 169.5, 169.3, 165.4, 165.1, 135.5, 134.5, 134.2,
133.6, 132.8, 131.4, 129.4, 129.4, 129.3, 129.1, 129.0, 128.9,
128.7, 128.6, 128.3, 128.3, 128.2, 127.6, 127.6, 126.9, 126.5,
126.4, 126.1, 125.6, 125.3, 125.2, 124.6, 124.6, 124.3, 122.9, 76.5,
76.5, 61.0, 60.9, 50.2, 47.5, 28.5, 20.2, 20.2, 19.3, 19.3; Anal. Calcd.
for C23H21NO3: C, 76.86; H, 5.89; N, 3.90. Found: C, 76.84; H, 5.84,
N, 3.91.
4.3.11. (10S,3R,4S)- and (10S,3S,4R)-1-(10-Phenylethyl)-3-
methoxy-4-phenyl-azetidin-2-one 3a/30a
IR (ATR) m
max 1746, 1648, 1521 cmꢀ1; 1H NMR (300 MHz, CDCl3,
Major isomer) d 7.05–7.29 (10H, m, ArH), 4.43 (1H, d, J = 4.5 Hz, C3-
H), 4.33 (1H, d, J = 4.5 Hz, C4-H), 4.13 (1H, q, J = 7.2 Hz, CHCH3),
2.99 (3H, s, OCH3), 1.73 (3H, d, J = 7.2 Hz, CHCH3); 1H NMR
(300 MHz, CDCl3, Minor isomer) d 7.05–7.29 (10H, m, ArH), 4.92
(1H, q, J = 7.5 Hz, CHCH3), 4.37 (1H, d, J = 4.5 Hz, C3-H), 4.28 (1H,
d, J = 4.5 Hz, C4-H), 3.03 (3H, s, OCH3), 1.24 (3H, d, J = 7.2 Hz,
CHCH3); 13C NMR (75 MHz, CDCl3, Both isomers) d 166.8, 140.9,
139.4, 135.1, 133.8, 128.8, 128.7, 128.6, 128.6, 128.5, 128.4,
128.2, 128.1, 127.9, 127.7, 127.3, 126.8, 84.8, 61.1, 61.0, 58.1,
58.0, 54.3, 51.8, 19.9, 19.1; Anal. Calcd. for C18H19NO2: C, 76.84;
H, 6.81; N, 4.98. Found: C, 76.80; H, 6.80; N, 4.95.
4.3.8. (10R, 3R, 4S)- and (10R, 3S, 4R)-1-(10-Naphthylethyl)-3-
acetoxy-4-styrylazetidin-2-one 2h/20h
IR (ATR) m
max 1750, 1652, 1599, 1512 cmꢀ1; 1H NMR (400 MHz,
CDCl3, Major isomer, Pure) d 7.18–7.52 (12H, m, ArH), 6.16 (1H, d,
J = 15.8 Hz, CH = CHPh), 5.98 (1H, dd, J = 15.8, 9.0 Hz, CH = CHPh),
5.79 (1H, q, J = 6.9 Hz, CHCH3), 5.49 (1H, d, J = 4.8 Hz, C3-H), 3.68
(1H, dd, J = 9.0, 4.8 Hz, C4-H), 1.95 (3H, s, CH3COO), 1.71 (3H, d,
J = 7.0 Hz, CHCH3); 1H NMR (300 MHz, CDCl3, Minor isomer, Pure)
d 6.73–8.11 (12H, m, ArH), 6.05 (1H, d, J = 15.9 Hz, CH = CHPh),
5.60 (1H, d, J = 4.8 Hz, C3-H), 5.40 (1H, q, J = 6.9 Hz, CHCH3), 5.27
(1H, dd, J = 15.9, 8.7 Hz, CH = CHPh), 4.22 (1H, dd, J = 8.7, 4.5 Hz,
C4-H), 1.87 (3H, s, CH3COO), 1.80 (3H, d, J = 7.2 Hz, CHCH3); 13C
NMR (100 MHz, CDCl3, Major isomer) d 169.3, 164.0, 136.5,
135.8, 133.9, 133.2, 131.1, 129.2, 129.1, 128.8, 128.5, 127.3,
126.6, 126.1, 124.9, 124.4, 123.1, 122.6, 76.1, 59.3, 47.0, 20.4,
19.1; 13C NMR (100 MHz, CDCl3, Both isomers) d 169.2, 164.2,
163.9, 136.3, 136.1, 135.7, 135.5, 134.6, 133.8, 133.1, 131.0,
129.0, 129.0, 128.9, 128.8, 128.6, 128.4, 128.2, 128.0, 127.1,
126.7, 126.5, 126.3, 126.0, 125.8, 125.1, 124.8, 124.3, 124.1,
123.0, 122.7, 122.5, 121.7, 77.1, 76.1, 76.0, 59.2, 59.0, 48.3, 46.9,
20.2, 19.0, 18.3; Anal. Calcd. for C25H23NO3: C, 77.90; H, 6.01; N,
3.63. Found: C, 77.84; H, 5.99; N, 3.60.
4.3.12. (10S,3R,4S)- and (10S,3S,4R)-1-(10-Phenylethyl)-3-
methoxy-4-(40-methoxyphenyl)azetidin-2-one 3b/30b
Yellow oil; IR (ATR) mmax 1750, 1615 cmꢀ1 1H NMR (300 MHz,
;
CDCl3, Major isomer) d 6.69–7.25 (9H, m, ArH), 4.40 (1H, d,
J = 4.5 Hz, C3-H), 4.29 (1H, d, J = 4.5 Hz, C4-H), 4.14 (1H, q,
J = 7.2 Hz, CHCH3), 3.72 (3H, s, OCH3), 3.04 (3H, s, OCH3), 1.72
(1H, d, J = 7.2 Hz, CHCH3); 1H NMR (300 MHz, CDCl3, Minor isomer)
d 6.69–7.25 (9H, m, ArH), 4.94 (1H, q, J = 7.2 Hz, CHCH3), 4.34 (1H,
d, J = 4.5 Hz, C3-H), 4.24 (1H, d, J = 4.5 Hz, C4-H), 3.73 (3H, s, OCH3),
3.00 (3H, s, OCH3), 1.24 (1H, d, J = 7.2 Hz, CHCH3); 13C NMR
(100 MHz, CDCl3, Both isomers) d 166.9, 166.8, 159.8, 159.7,
141.0, 139.5, 130.0, 129.8, 128.7, 128.6, 127.9, 127.7, 127.3,
126.9, 126.8, 125.6, 113.7, 113.5, 84.8, 60.5, 60.4, 58.1, 58.0, 55.2,
54.1, 51.6, 19.9, 19.1; Anal. Calcd. for C19H21NO3: C, 73.29; H,
6.80; N, 4.50. Found: C, 73.25; H, 6.78; N, 4.52.