D. B. Llewellyn, B. A. Arndtsen / Tetrahedron: Asymmetry 16 (2005) 1789–1799
1797
5aÆ2CH3CN. Yield = 97%. 1H NMR: (270 MHz,
CD3CN): d 8.59 (d, 4H), 7.29–7.52 (m, 20H), 5.42 (d,
4H), 4.04 (s, 4H), 3.60 (s, 12H). 13C NMR: (68 MHz,
CD3CN): d 174.5, 171.0, 136.9, 128.8, 128.3, 127.5,
78.9, 56.7, 52.2. 11B NMR: (87 MHz, CD3CN): d
11.87. IR: (KBr): mCO = 1740 cmꢀ1 (ester), 1646 cmꢀ1
(amide). LRMS: M+ = 959. Elemental Analysis: Calcu-
lated for C48H50BCuN6O16: C, 55.36; H, 4.84; N, 8.07.
Found: C, 55.40; H, 5.14; N, 7.78. 5bÆCH3CN.
Yield = 94%. 1H NMR: (270 MHz, CD3CN): d 8.67
(d, 4H), 7.10–7.60 (m, 40H), 5.46 (d, 4H), 5.08 (d,
4H), 5.02 (d, 4H), 4.03 (s, 4H). 13C NMR: (68 MHz,
CD3CN): 174.6, 170.4, 136.7, 136.0, 128.8, 128.4,
128.3, 128.1, 127.7, 127.6, 78.9, 66.6, 56.9. 11B NMR:
(87 MHz, CD3CN): d 12.09. 5cÆCH3CN. Yield = 94%.
1H NMR: (270 MHz, d6-DMSO): d 8.70 (d, 4H), 7.28–
7.50 (m, 20H), 5.44 (d, 4H), 4.60 (m, 4H), 4.02 (s, 4H),
1.19–1.70 (m, 44H). 13C NMR: (68 MHz, d6-DMSO):
d 174.4 (br), 169.8, 137.6, 128.9, 128.4, 127.5, 78.9
(br), 73.4, 56.8, 31.0, 30.9, 25.1, 23.2, 23.1. 11B NMR:
(87 MHz, d6-DMSO): d 12.7. 5dÆCH3CN. Yield = 95%.
1H NMR: (270 MHz, d6-DMSO): d 8.39 (d, 4H), 7.20–
7.50 (m, 20H), 5.02 (m, 4H), 4.03 (s, 4H), 3.50–3.60
(m, 8H), 3.16 (s, 12H). 13C NMR: (68 MHz, d6-DMSO):
d 174.5 (br), 141.2, 128.6, 127.3, 127.3, 78.9 (br), 76.0,
58.6, 52.6. 11B NMR: (87 MHz, d6-DMSO): d 12.00
5eÆ2CH3CN. Yield = 85%. 1H NMR: (270 MHz,
CD3CN): d 8.75 (d, 4H), 7.20–7.5 (m, 24H), 5.35 (d,
4H), 4.13 (s, 4H), 2.97 (m, 4H), 2.93 (m, 4H), 1.12–
1.40 (m, 16H), 0.77 (t, 12H). 13C NMR: (68 MHz,
CD3CN): d 174.7, 170.5, 138.5, 128.5, 127.7, 127.0,
79.0, 57.9, 39.0, 31.2, 19.7, 13.1. 11B NMR: (87 MHz,
1H NMR: (270 MHz, CD3CN): d 8.54 (d, 4H), 7.28
(m, 20H), 5.18 (d, 4H), 4.20 (s, 4H), 3.59 (s, 12H). 13C
NMR: (68 MHz, CD3CN): d 174.9, 171.0, 136.6,
128.7, 128.2, 127.5, 78.5, 56.9, 52.1. 11B NMR:
(87 MHz,
m
CD3CN):
d
12.05.
IR:
(KBr):
CO = 1743 cmꢀ1 (ester), 1673 (amide). LRMS:
M+ = 959. Elemental Analysis: Calculated for
C46H47BCuN5O16: C, 55.24; H, 4.74; N, 7.00. Found:
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C, 55.01; H, 4.74; N, 7.17. 5lÆCH3CN. Yield = 90%. H
NMR: (270 MHz, d6-DMSO): d 8.06 (d, 4H), 7.10–
7.40 (m, 20H), 4.51 (m, 4H), 3.89 (s, 4H), 3.55 (s,
12H), 3.06 (dd, 4H), 2.91 (dd, 4H). 13C NMR:
(68 MHz, d6-DMSO): d 174.5 (br), 172.1, 137.5, 129.9,
128.6, 127.0, 78.2 (br), 53.8, 52.4, 38.1. 11B NMR:
(87 MHz,
d6-DMSO):
d
11.83.
5mÆCH3CN.
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Yield = 98%. H NMR: (270 MHz, d6-DMSO): d 7.94
(d, 4H), 4.22 (dd, 4H), 4.03 (s, 4H), 3.59 (s, 12H), 2.09
(m, 4H), 0.89 (d, 12H), 0.85 (d, 12H). 13C NMR:
(68 MHz, d6-DMSO): d 174.8, 172.0, 79.4, 57.5, 52.2,
31.1, 19.2, 17.8. 11B NMR: (87 MHz, d6-DMSO): d
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12.01. 5nÆCH3CN. Yield = 90%. H NMR: (270 MHz,
d6-DMSO): d 8.06 (d, 4H), 7.18–7.40 (m, 20H), 4.51
(m, 4H), 3.89 (s, 4H), 3.55 (s, 12H), 3.06 (dd, 4H),
2.91 (dd, 4H). 13C NMR: (68 MHz, d6-DMSO): d
174.5 (br), 172.1, 137.5, 129.9, 128.6, 127.0, 78.2 (br),
53.8, 52.4, 38.1. 11B NMR: (87 MHz, d6-DMSO): d
11.8 5oÆ2CH3CN. Yield = 79%. 1H NMR: (270 MHz,
CD3CN): d 8.66 (d, 4H), 7.42 (d, 4H), 7.28–7.50 (m,
20H), 5.43 (d, 4H), 4.20 (m, 8H), 3.52 (s, 12H), 1.20
(d, 12H). 13C NMR: (68 MHz, CD3CN): 174.8, 172.6,
170.1, 137.9, 128.4, 127.8, 127.3, 78.6, 57.1, 51.7, 48.2,
16.6. 11B NMR: (87 MHz, CD3CN): 11.87 5pÆ4CH3CN.
1
1
CD3CN): d 11.85 5fÆ2CH3CN. Yield = 97%. H NMR:
Yield = 87%. H NMR: (270 MHz, d6-DMSO): d 8.65
(270 MHz, d6-DMSO): d 10.84 (s, 4H), 8.14 (d, 4H),
7.50 (d, 4H), 7.29–7.32 (m, 8H), 6.93–7.07 (m, 8H),
4.51 (m, 4H), 4.09 (s, 4H), 3.47 (s, 12H), 3.16 (m, 8H).
13C NMR: (68 MHz, d6-DMSO): d 174.7, 172.6, 136.6,
127.6, 124.8, 121.3, 118.8, 118.4, 111.9, 109.5, 78.2,
53.6, 52.3, 28.0. 11B NMR: (87 MHz, d6-DMSO): d
(d, 4H), 8.36 (d, 4H), 7.50 (m, 8H), 7.22 (m, 12H),
5.61 (d, 4H), 4.10 (m, 4H), 4.09 (s, 4H), 3.48 (s, 12H),
1.91 (m, 4H), 0.81 (d, 12H), 0.78 (d, 12H). 13C NMR:
(68 MHz, d6-DMSO): d 174.6, 172.0, 170.2, 138.8,
128.4, 127.6, 127.5, 78.6, 58.0, 56.3, 52.0, 30.3, 19.3,
18.8. 11B NMR: (87 MHz, d6-DMSO):
d 11.70.
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11.80. 5gÆCH3CN. Yield = 87%. H NMR: (270 MHz,
5qÆ2CH3CN. Yield = 80%. 1H NMR: (270 MHz, d6-
DMSO): d 8.58 (m, 8H), 7.0–7.45 (m, 40H), 5.51 (d,
4H), 4.41 (m, 4H), 4.09 (br s, 4H), 3.41 (s, 12H), 2.89
(s, 4H), 2.86 (s, 4H). 13C NMR: (68 MHz, CD3CN): d
174.5 (br), 171.4, 170.2, 137.7, 136.9, 129.4, 128.5,
128.4, 127.8, 127.5, 126.7, 78.4, 57.2, 54.0, 51.7, 36.9.
11B NMR: (87 MHz, d6-DMSO): d 11.75. IR: (KBr):
CD3CN): d 7.91 (br s, 4H), 4.43 (m, 4H), 4.13 (s, 4H),
3.66 (m, 12H), 3.58 (s, 12H), 2.41 (m, 8H), 2.10 (m,
4H), 1.94 (m, 4H). 13C NMR: (68 MHz, CD3CN): d
175.0, 173.1, 172.4, 78.4, 51.9, 51.2, 51.2, 29.3, 26.8.
11B NMR: (87 MHz, CD3CN): d 11.9. 5hÆCH3CN.
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Yield = 97%. H NMR: (270 MHz, d6-DMSO): d 8.91
(d, 4H), 4.20 (d, 4H), 4.02 (s, 4H), 3.56 (s, 12H), 0.91
(s, 36H). 13C NMR: (68 MHz, d6-DMSO): d 174.3,
171.2, 80.2, 60.7, 51.8, 35.1, 26.7. 11B NMR: (87 MHz,
m
CO = 1743 cmꢀ1 (ester), 1659 cmꢀ1 (amides). Elemental
Analysis: Calculated for C84H86BcuN10O20: C, 61.90; H,
5.32; N, 8.59. Found: C, 61.56; H, 5.34; N, 8.41.
5rÆ2CH3CN. Yield = 92%. 1H NMR: (270 MHz,
CD3CN): d 8.69 (d, 4H), 7.80 (d, 4H), 7.20–7.50 (m,
40H), 5.48 (d, 4H), 5.29 (d, 4H), 4.15 (s, 4H), 3.49 (s,
12H). 13C NMR: (68 MHz, CD3CN): d 174.8, 170.7,
170.0, 137.7, 136.4, 128.9, 128.7, 128.4, 128.2, 127.5,
127.4, 78.5, 57.1, 56.5, 52.1. 11B NMR: (87 MHz,
d6-DMSO):
d
12.10. 5iÆCH3CN. Yield = 93%. 1H
NMR: (270 MHz, d6-DMSO): d 8.09 (br s, 4H), 4.03
(br s, 4H), 3.98 (br s, 4H), 3.60 (s, 12H), 0.92 (s, 36H).
13C NMR: (68 MHz, d6-DMSO): d 174.7 (broad),
171.5, 78.2 (broad), 61.4, 51.8, 34.1, 27.0. 11B NMR:
(87 MHz, d6-DMSO): d 11.86. 5jÆCH3CN. Yield = 99%.
1H NMR: (270 MHz, CD3CN): d 7.99 (br s, 4H), 4.17 (s,
4H), 3.98 (s, 4H), 3.96 (s, 4H), 3.67 (s, 12H). 13C NMR:
(68 MHz, CD3CN): d 175.5, 170.9, 77.6, 51.8, 40.7. 11B
CD3CN):
d
11.62. 5sÆ2CH3CN. Yield = 87%. 1H
NMR: (270 MHz, CD3CN): d 8.57 (d, 4H), 7.78 (d,
4H), 7.14–7.50 (m, 40H), 5.47 (d, 4H), 5.40 (d, 4H),
4.06 (s, 4H), 3.58 (s, 12H). 13C NMR: (68 MHz,
CD3CN): d 174.8, 170.8, 170.0, 137.8, 136.4, 128.7,
128.5, 128.3, 127.8, 127.4, 127.3, 78.5, 57.3, 56.4, 52.3.
11B NMR: (87 MHz, CD3CN): d 11.7. 5tÆ2CH3CN.
NMR: (87 MHz, CD3CN):
d
11.39. IR: (KBr):
m
CO = 1748 cmꢀ1 (ester),
m
CO = 1656 cmꢀ1 (amide).
LRMS: M+ = 655. Elemental Analysis: Calculated for
C22H47BCuN5O16: C, 37.97; H, 4.49; N 10.06. Found:
C, 37.97; H 4.45; N, 10.15. 5kÆCH3CN. Yield = 88%.
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Yield = 91%. H NMR: (270 MHz, CD3CN): 7.97 (d,