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HETEROCYCLES, Vol. 83, No. 1, 2011
PMP, 5o), 118.64 (C2 and C6, PMP, 5o/6o), 125.85 (C2 and C6, Ph, β-lactam, 5o), 125.95 (C2 and C6,
Ph, β-lactam, 6o), 128.12 (C4, Ph, β-lactam, 6o), 128.22 (C4, Ph, β-lactam, 5o), 128.73 (C3 and C5, Ph,
β-lactam, 6o), 129.00 (C3 and C5, Ph, β-lactam, 5o), 131.00 (C1, Ph, β-lactam, 6o), 131.03 (C1, Ph, β-
lactam, 5o), 137.15 (C1, PMP, 6o), 137.31 (C1, PMP, 5o), 150.32 (C2, furan, 5o), 151.36 (C2, furan, 6o),
151.75 (C5, furan, 6o), 151.85 (C5, furan, 5o), 156.06 (C4, PMP, 6o), 156.06 (C4, PMP, 5o), 164.96 (CO,
β-lactam, 5o), 165.33 (CO, β-lactam, 6o), 177.03 (COOMe, 6o), 177.33 (COOMe, 5o). HRMS for
C27H30N2O5 (5o/6o, Mr = 462.54838): calcd. m/z [M+Na]+ 485.2047, found 485.2061.
Methyl (3S/3R)-(trans-(3’R,4’R)-3-amino-4-ferrocenyl-1-(4-methoxyphenyl)-2-oxoazetidin-3-yl)-2,2-
dimethyl-3-phenylpropanoate, 5q/6q
Obtained from (3R,4R)-3q (15.0 mg, 3.23 x 10-2 mmol), silylenol ether 4 (6.19 mg, 7.20 μL, 3.55 x 10-2
mmol) and zinc(II) iodide (10.3 mg, 3.23 x 10-2 mmol) as a diastereomeric mixture 5q/6q, 8.80 mg
(48.1%), Rf = 0.27 (EtOAc – petroleum ether in ratio 1:4). RP-HPLC analysis (method III) of
diastereomeric mixture showed ratio of 5q/6q – 59:41% (5q, 3.12 min and 6q, 3.95 min). IR (KBr)
νmax/cm1: 3630, 3468, 2925, 1735, 1685, 1654, 1637, 1560, 1542, 1508, 1458, 1246, 705; 1H NMR (300
MHz, CDCl3) δ/ppm: 1.13 (s, 3H, CMe2, 5q), 1.15 (s, 3H, CMe2, 6q), 1.21 (s, 3H, CMe2, 6q), 1.22 (s, 3H,
CMe2, 5q), 2.59 (bs, 2H, NH, β-lactam, 5q/6q), 3.71 (s, 3H, COOMe, 6q), 3.73 (s, 3H, COOMe, 5q),
3.74 (s, 3H, OMe, PMP, 6q), 3.77 (s, 3H, OMe, PMP, 5q), 3.83-3.84 (m, 1H, Fc, 6q), 3.85-3.87 (m, 1H,
Fc, 5q), 3.90-3.91 (m, 1H, Fc, 5q), 3.99 (d, 1H, J = 1.92 Hz, C4, β-lactam, 6q), 4.03 (s, 5H, Fc, 5q), 4.05-
4.08 (m, 4H, Fc, 5q/6q), 4.09 (s, 5H, Fc, 6q), 4.10 (s, 1H, Fc, 6q), 4.13 (s, 1H, Fc, 5q), 4.15 (d, 1H, J =
2.67 Hz, C4, β-lactam, 5q), 4.28 (s, 1H, CHN, 6q), 4.30 (d, 1H, J = 1.65 Hz, C3, β-lactam, 5q), 4.50 (d,
1H, J = 2.01 Hz, C3, β-lactam, 6q), 4.53 (s, 1H, CHN, 5q), 6.79 (d, 2H, J = 9.03 Hz, C3 and C5, PMP,
6q), 6.83 (d, 2H, J = 9.00 Hz, C3 and C5, PMP, 5q), 7.22-7.24 (m, 4H, C2 and C6, PMP, 5q/6q), 7.26 (s,
13
5H, Ph, 5q), 7.40 (s, 5H, Ph, 6q); C NMR (75 MHz, CDCl3) δ/ppm: 19.33 (CMe2, 5q), 20.07 (CMe2,
6q), 24.09 (CMe2, 6q), 24.30 (CMe2, 5q), 47.22 (CMe2, 6q), 47.44 (CMe2, 5q), 52.06 (COOMe, 5q/6q),
55.42 (OMe, PMP, 6q), 55.45 (OMe, PMP, 5q), 59.45 (C4, β-lactam, 5q), 59.90 (C4, β-lactam, 6q),
66.15 (C3, β-lactam, 5q), 66.21 (C3, β-lactam, 6q), 66.58 (Fc, 5q), 66.78 (Fc, 6q), 67.57 (Fc, 5q), 67.80
(Fc, 6q), 68.32 (Fc, 6q), 68.48 (Fc, 5q), 68.53 (Fc, 5q), 68.61 (Fc, 5q), 68.80 (Fc, 6q), 69.43 (Fc, 5q),
70.74 (CHN, 6q), 72.01 (CHN, 5q), 84.29 (C1, Fc, 6q), 85.92 (C1, Fc, 5q), 114.15 (C3 and C5, PMP, 6q),
114.19 (C3 and C5, PMP, 5q), 119.23 (C2 and C6, PMP, 6q), 119.85 (C2 and C6, PMP, 5q), 127.89 (C4,
Ph, 6q), 127.92 (C4, Ph, 5q), 128.04 (C2 and C6, Ph, 6q), 128.16 (C2, C6, Ph, 5q), 129.15 (C3 and C5,
Ph, 5q), 129.48 (C3 and C5, Ph, 6q), 130.65 (C1, Ph, 5q), 130.97 (C1, Ph, 6q), 138.92 (C1, PMP, 6q),
139.11 (C1, PMP, 5q), 156.12 (C4, PMP, 6q), 156.38 (C4, PMP, 5q), 165.97 (CO, β-lactam, 5q), 166.77