6
A.K. Padala et al. / Tetrahedron xxx (2015) 1e8
3
H); 13C NMR (CDCl3, 126 MHz)
d
166.80, 163.32, 131.55, 122.56,
(CDCl3, 126 MHz) d 168.05, 133.88, 133.43, 131.39, 130.29, 128.59,
113.57, 55.33, 51.78.
127.81, 127.08, 126.25, 125.87, 124.53, 52.17.
4
4
.4.9. Methyl 1H-indole-2-carboxylate (5i).7e 1H NMR (CDCl3,
00 MHz)
9.20 (s, 1H), 7.69 (d, J¼8.0 Hz,1H), 7.42 (d, J¼8.3 Hz, 1H),
4.4.20. Methyl 4-chlorobenzoate (5t).7c 1H NMR (CDCl3, 500 MHz)
13
d
d
7.83 (d, J¼8.3 Hz, 2H), 7.26 (d, J¼8.3 Hz, 2H), 3.78 (s, 3H); C NMR
7
(
.32 (t, J¼7.3 Hz, 1H), 7.25e7.21 (m, 1H), 7.15 (t, J¼7.4 Hz, 1H), 3.95
(CDCl3, 126 MHz) 166.13, 139.31, 130.94, 128.67, 128.55, 52.22.
d
s, 3H); 13C NMR (CDCl3, 126 MHz)
d
161.68, 135.97, 126.42, 126.05,
124.40, 121.62, 119.79, 110.96, 107.81, 51.07.
4.4.21. Ethyl 4-bromobenzoate (5u).7c 1H NMR (CDCl3, 400 MHz)
d
7.90 (d, J¼8.5 Hz, 2H), 7.57 (d, J¼8.5 Hz, 2H), 4.37 (q, J¼7.1 Hz, 2H),
13
4
4
3
5
.4.10. Methyl 5-nitrofuran-2-carboxylate (5j).7o 1H NMR (CDCl3,
00 MHz)
1.39 (t, J¼7.1 Hz, 3H); C NMR (CDCl3, 126 MHz)
d 165.85, 131.64,
d
7.36 (d, J¼3.8 Hz, 1H), 7.31 (d, J¼3.8 Hz, 1H), 3.98 (s,
131.08, 129.39, 127.89, 61.23, 14.29.
13
H); C NMR (CDCl3, 126 MHz)
2.98.
d 157.42, 144.74, 118.95, 111.61,
4.4.22. Isopropyl 3-methylbenzoate (5v).7d 1H NMR (CDCl3,
00 MHz) 7.90e7.79 (m, 2H), 7.37e7.27 (m, 2H), 5.25 (hept,
J¼6.3 Hz, 1H), 2.39 (s, 3H), 1.36 (d, J¼6.3 Hz, 6H). C NMR (CDCl3,
101 MHz) 166.28, 138.00, 133.42, 130.88, 130.02, 128.15, 126.65,
4
d
4
.4.11. Methyl (E)-3-(3-methoxyphenyl)acrylate (5k).7h 1H NMR
7.64 (d, J¼16.0 Hz, 1H), 7.26 (t, J¼7.9 Hz, 1H),
.08 (d, J¼7.6 Hz, 1H), 7.01 (s, 1H), 6.91 (dd, J¼8.2, 1.8 Hz, 1H), 6.41
13
(
CDCl3, 400 MHz)
d
d
7
68.21, 21.94, 21.24.
13
(
d, J¼16.0 Hz, 1H), 3.79 (s, 3H), 3.78 (s, 3H); C NMR (CDCl3,
126 MHz) 167.38, 159.87, 144.81, 135.69, 129.88, 120.74, 118.02,
d
4.4.23. Butyl 3-methylbenzoate (5w).7b 1H NMR (CDCl3, 500 MHz)
1
16.10, 113.01, 55.20, 51.69.
d
7.85 (m, 2H), 7.33 (m, 2H), 4.31 (t, J¼6.6 Hz, 2H), 2.40 (s, 3H), 1.75
13
(
dt, J¼14.5, 6.6 Hz, 2H), 1.53e1.44 (m, 2H), 0.98 (t, J¼7.4 Hz, 3H). C
4
.4.12. Methyl (2E,4E)-5-(benzo[d][1,3]dioxol-5-yl)penta-2,4-
NMR (CDCl3, 126 MHz) 165.83, 137.03, 132.49, 129.42, 129.01,
d
7p 1
dienoate (5l).
H NMR (CDCl3, 400 MHz)
d
7.41 (dd, J¼15.2,
127.16, 125.62, 63.72, 29.76, 20.22, 18.23, 12.71.
1
0.8 Hz, 1H), 6.98 (d, J¼1.1 Hz, 1H), 6.90 (d, J¼8.0 Hz, 1H), 6.78 (dd,
J¼11.7, 6.7 Hz, 2H), 6.68 (dd, J¼15.4, 10.8 Hz, 1H), 5.97 (s, 2H), 5.93
4.4.24. Allyl 2-(3-nitrophenyl)acetate (5x).7k 1H NMR (CDCl3,
400 MHz)
13
(
1
d, J¼15.3 Hz, 1H), 3.76 (s, 3H); C NMR (CDCl3, 126 MHz)
d
167.59,
d
8.18 (d, J¼8.5 Hz, 2H), 7.47 (d, J¼8.4 Hz, 2H), 5.90 (dq,
48.58, 148.29, 145.01, 140.30, 130.52, 124.46, 123.01, 119.91, 108.52,
J¼10.7, 5.8 Hz, 1H), 5.26 (dd, J¼19.5, 13.8 Hz, 2H), 4.62 (d, J¼5.7 Hz,
13
105.85, 101.42, 51.53.
2H), 3.78 (s, 2H); C NMR (CDCl3, 126 MHz)
31.64, 130.35, 123.72, 118.75, 65.91, 40.88.
d 169.84, 147.18, 141.29,
1
4
4
3
.4.13. Methyl 2-(4-nitrophenyl)acetate (5m).7l 1H NMR (CDCl3,
00 MHz)
8.18 (d, J¼8.6 Hz, 2H), 7.47 (d, J¼8.6 Hz, 2H), 3.76 (s, 2H),
.73 (s, 3H); C NMR (CDCl3, 126 MHz)
d
4.4.25. Benzyl 2-(4-nitrophenyl)acetate (5y).7k 1H NMR (CDCl3,
400 MHz)
8.16 (d, J¼8.6 Hz, 2H), 7.44 (d, J¼8.4 Hz, 2H), 7.38e7.29
(m, 5H), 5.15 (s, 2H), 3.77 (s, 2H); C NMR (CDCl3, 126 MHz)
170.04, 147.22, 141.23, 135.41, 130.37, 128.68, 128.54, 128.35,
13
d
170.67, 147.10, 141.40,
d
13
130.36, 123.67, 52.36, 40.66.
d
4
.4.14. Methyl decanoate (5n).7g 1H NMR (CDCl3, 400 MHz)
d
3.66
123.76, 67.17, 40.96.
(
1
5
s, 3H), 2.30 (t, J¼7.5 Hz, 2H), 1.61 (dd, J¼14.4, 7.2 Hz, 2H), 1.28 (m,
13
2H), 0.88 (t, J¼6.8 Hz, 3H); C NMR (CDCl3, 126 MHz)
d
174.27,
4.4.26. (S)-(2,2-Dimethyl-1,3-dioxolan-4-yl)methyl 2-(3-
1
1.36, 34.06, 31.85, 29.40, 29.25, 29.13, 24.93, 22.64, 14.05.
nitrophenyl)acetate (5z). H NMR (CDCl3, 400 MHz)
d
8.13 (d,
J¼8.6 Hz, 2H), 7.40 (d, J¼8.6 Hz, 2H), 4.29e4.22 (m, 1H), 4.15 (dd,
J¼11.5, 4.3 Hz, 1H), 4.08 (dd, J¼11.5, 6.0 Hz, 1H), 3.99 (dd, J¼8.4,
6.6 Hz, 1H), 3.72 (s, 2H), 3.64 (dd, J¼8.5, 6.1 Hz, 1H), 1.34 (s, 3H), 1.30
4
.4.15. Methyl 6-(((benzyloxy)carbonyl)amino)hexanoate (5o). 1
7.32e7.22 (m, 5H), 5.13 (s, 1H), 5.06 (s, 2H),
.62 (s, 3H), 3.14 (dd, J¼12.6, 6.3 Hz, 2H), 2.27 (t, J¼7.3 Hz, 2H), 1.60
dt, J¼14.7, 7.3 Hz, 2H), 1.46 (dd, J¼14.1, 7.0 Hz, 2H), 1.31 (dd, J¼15.0,
.1 Hz, 2H); 13C NMR (CDCl3, 126 MHz)
174.13, 156.60, 136.71,
H
NMR (CDCl3, 400 MHz)
3
(
8
d
13
(s, 3H); C NMR (CDCl3, 126 MHz) d 170.05, 147.26, 140.97, 130.37,
123.81, 110.00, 73.41, 66.09, 65.55, 40.72, 26.67, 25.31; HRMS (ESI)
þ
d
Calcd for C14
H17NaNO
6
: [MþNa] , 318.0948; Found: 318.0953.
128.46, 128.36, 128.02, 127.28, 126.86, 66.46, 51.49, 40.78, 33.84,
þ
4.4.27. Butyl 3-mercaptopropanoate (5aa). 1
500 MHz)
4.00 (dd, J¼9.3, 4.0 Hz, 2H), 2.65 (m, 2H), 2.53 (t,
2
3
9.54, 26.17, 24.49; HRMS (ESI) Calcd for C15
02.1363; Found: 302.1357.
H
21NaNO
4
: [MþNa] ,
H
NMR (CDCl3,
d
J¼6.8 Hz, 2H), 1.57e1.44 (m, 3H), 1.32e1.24 (m, 2H), 0.84e0.79 (m,
4
d
.4.16. Methyl 4-bromobenzoate (5p).7c 1H NMR (CDCl3, 400 MHz)
3H); C NMR (CDCl3, 126 MHz)
13
d
171.72, 64.60, 38.51, 30.61, 19.79,
13
þ
7.89 (d, J¼8.5 Hz, 2H), 7.57 (d, J¼8.5 Hz, 2H), 3.91 (s, 3H); C NMR
19.12,13.70; HRMS (ESI) Calcd for C
Found: 185.0602.
7
H
14
O
2
NaS: [MþNa] ,185.0607;
(
CDCl3, 126 MHz)
d
164.31, 129.68, 129.08, 127.00, 126.01, 50.26.
4
d
.4.17. Methyl 3-nitrobenzoate (5q).7f 1H NMR (CDCl3, 400 MHz)
8.82 (s, 1H), 8.41 (ddd, J¼18.7, 9.8, 4.4 Hz, 2H), 7.69 (t, J¼8.0 Hz,
4.4.28. 2-Methylallyl 2-(4-nitrophenyl)acetate (5ab). 1
(CDCl3, 400 MHz)
8.18 (d, J¼8.7 Hz, 2H), 7.48 (d, J¼8.7 Hz, 2H), 4.92
(s, 2H), 4.54 (s, 2H), 3.79 (s, 2H), 1.72 (s, 3H); C NMR (CDCl3,
H
NMR
d
H), 4.00 (s, 3H); 13C NMR (CDCl3, 126 MHz)
d 164.86,148.16,135.23,
13
1
1
31.77, 129.68, 127.33, 124.45, 52.76.
126 MHz)
d
169.85, 147.13, 141.36, 139.44, 130.37, 123.70, 113.32,
þ
6
8.47, 40.92, 19.42; HRMS (ESI) Calcd for C12
H
13NaNO
4
: [MþNa] ,
4
d
.4.18. Methyl 3-methylbenzoate (5r).5b 1H NMR (CDCl3, 400 MHz)
7.85 (d, J¼5.1 Hz, 1H), 7.82 (s, 1H), 7.33 (dt, J¼15.0, 7.5 Hz, 2H), 3.90
258.0737; Found: 258.0721.
13
4.4.29. Ethyl decanoate (5ac).7i 1H NMR (CDCl3, 400 MHz)
J¼7.1 Hz, 2H), 2.26 (t, J¼7.6 Hz, 2H),1.64e1.56 (m, 2H),1.30e1.21 (m,
(
s, 3H), 2.39 (s, 3H); C NMR (CDCl3, 126 MHz)
d
167.30, 138.14,
d 4.10 (q,
133.67, 130.13, 130.09, 128.26, 126.71, 52.04, 21.26.
13
1
5H), 0.86 (t, J¼6.9 Hz, 3H); C NMR (CDCl3, 126 MHz)
d 173.84,
4
d
.4.19. Methyl 2-naphthoate (5s).1h 1H NMR (CDCl3, 400 MHz)
8.99e8.93 (m, 1H), 8.20 (dd, J¼7.3, 1.2 Hz, 1H), 8.01 (d, J¼8.2 Hz,
H), 7.88 (d, J¼8.2 Hz, 1H), 7.63 (ddd, J¼8.5, 6.8, 1.4 Hz, 1H),
60.08, 34.35, 31.84, 29.40, 29.25, 29.13, 24.97, 22.64, 14.21, 14.05.
1
4.4.30. Isopropyl decanoate (5ad).7j 1H NMR (CDCl3, 400 MHz)
13
7.56e7.52 (m, 1H), 7.49 (dd, J¼8.1, 7.4 Hz, 1H), 4.01 (s, 3H); C NMR
d
5.04e4.92 (m, 1H), 2.23 (t, J¼7.5 Hz, 2H), 1.58 (dd, J¼14.6, 7.3 Hz,