Z.-F. Zhang, Z.-H. Gao, C.-L. Zhang et al.
Tetrahedron 94 (2021) 132337
(s, 3H), 2.17 (m, 1H), 2.06e1.87 (m, 1H), 1.27 (tt, J ¼ 6.7, 4.9 Hz, 1H),
1.00 (d, J ¼ 6.9 Hz, 1H), 0.62 (d, J ¼ 6.9 Hz, 3H); 13C NMR (126 MHz,
4.1.16. Phenyl 2-((5S)-5-(((tert-butyldiphenylsilyl)oxy)methyl)-1-
((4-nitrophenyl)sulfonyl)pyrrolidin-2-yl)acetate (2p)
CDCl3)
d
170.0, 150.6, 143.6, 133.7, 129.7, 129.6, 129.4, 127.7, 125.9,
99.1 mg, 75% yield, dr ¼ 5:1; Colorless oil; Rf ¼ 0.23 (petroleum
121.6, 63.8, 47.6, 41.0, 39.1, 31.0, 21.5, 18.1. IR (KBr) 1754, 1644, 1344,
1162, 689; HRMS (ESI) calcd for C20H23NNaSO4 [MþNa]þ: 396.1240,
found 396.1236.
ether/ethyl acetate 4:1).1H NMR (500 MHz, CDCl3)
d 8.33 (d,
J ¼ 8.7 Hz, 2H), 7.93 (d, J ¼ 8.7 Hz, 2H), 7.68 (d, J ¼ 7.4 Hz, 4H),
7.51e7.46 (m, 2H), 7.46e7.39 (m, 5H), 7.37 (d, J ¼ 8.1 Hz, 1H), 7.23 (d,
J ¼ 7.5 Hz, 1H), 7.09 (d, J ¼ 7.8 Hz, 2H), 4.04e3.96 (m, 1H), 3.90 (dd,
J ¼ 10.4, 3.7 Hz, 1H), 3.73 (dt, J ¼ 12.8, 6.3 Hz, 1H), 3.63 (m, 1H), 3.30
(dd, J ¼ 16.5, 4.7 Hz, 1H), 2.76 (dd, J ¼ 16.5, 8.5 Hz, 1H), 1.85 (m 1H),
4.1.12. Phenyl 2-(3-allyl-1-tosylpyrrolidin-2-yl)acetate (2l)
40.1 mg, 50% yield, dr ¼ 4:1; Colorless oil; Rf ¼ 0.23 (petroleum
1.74 (m, 1H), 1.10 (s, 9H); 13C NMR (126 MHz, CDCl3)
d 169.7, 150.4,
ether/ethyl acetate 4:1). 1H NMR (500 MHz, CDCl3)
d 7.78 (t,
150.2, 142.8, 135.7, 135.7, 135.5, 133.3, 132.9, 129.9, 129.7, 129.5,
128.9, 127.8, 126.0, 124.4, 121.5, 115.3, 65.9, 62.6, 58.3, 41.6, 30.6,
26.9, 26.8, 26.6, 19.3. IR (KBr) 1755, 1531, 1350, 1164, 703; HRMS
J ¼ 6.2 Hz, 2H), 7.38 (t, J ¼ 7.9 Hz, 2H), 7.33 (t, J ¼ 6.6 Hz, 2H), 7.24 (t,
J ¼ 7.4 Hz, 1H), 7.11 (d, J ¼ 7.7 Hz, 2H), 5.53 (ddt, J ¼ 17.1, 10.1, 7.0 Hz,
1H), 4.91 (d, J ¼ 10.1 Hz, 1H), 4.71 (dd, J ¼ 17.0, 1.4 Hz, 1H), 3.75 (dt,
J ¼ 8.9, 3.4 Hz, 1H), 3.55e3.48 (m, 1H), 3.29e3.21 (m, 1H), 3.19 (td,
J ¼ 9.3, 7.1 Hz, 1H), 2.87e2.77 (m, 1H), 2.44 (s, 3H), 2.19e2.11 (m,
1H), 2.05e1.95 (m, 1H), 1.67 (dt, J ¼ 14.0, 7.0 Hz, 1H), 1.51 (dd,
J ¼ 14.7, 7.5 Hz, 1H), 1.44 (ddd, J ¼ 10.8, 7.4, 4.1 Hz, 1H); 13C NMR
(ESI) calcd for
681.2058.
C
35H38N2NaSSiO7 [MþNa]þ: 681.2061, found
4.1.17. Phenyl 2-(1-tosylindolin-2-yl)acetate (2q)
75.7 mg, 93% yield; Colorless oil; Rf ¼ 0.43 (petroleum ether/
(126 MHz, CDCl3)
d 169.8, 150.5, 143.7, 135.3, 134.0, 129.7, 129.4,
ethyl acetate 4:1). 1H NMR (500 MHz, CDCl3)
d
7.63 (d, J ¼ 8.1 Hz,
127.6, 125.9, 121.6, 117.0, 61.0, 47.4, 43.8, 41.3, 36.7, 28.4, 21.5. IR
(KBr) 1752, 1592, 1344, 1191, 688; HRMS (ESI) calcd for
1H), 7.51 (d, J ¼ 8.2 Hz, 2H), 7.34e7.25 (m, 3H), 7.18e7.14 (m, 2H),
7.11 (d, J ¼ 7.9 Hz, 2H), 7.04 (d, J ¼ 7.8 Hz, 1H), 6.99 (dd, J ¼ 16.8,
7.8 Hz, 4H), 4.61 (ddd, J ¼ 13.0, 9.3, 3.7 Hz, 1H), 3.25 (dd, J ¼ 16.4,
4.3 Hz, 1H), 2.99e2.92 (m, 1H), 2.86 (dd, J ¼ 16.4, 9.6 Hz, 1H),
C
22H25NNaSO4 [MþNa]þ: 422.1397, found 422.1393.
4.1.13. Phenyl 2-(2-tosyl-2-azaspiro[4.5]decan-3-yl)acetate (2m)
64.5 mg, 76% yield; White solid, m.p. ¼ 97e98 ꢁC; Rf ¼ 0.23
(petroleum ether/ethyl acetate 4:1).1H NMR (500 MHz, CDCl3)
2.69e2.62 (m, 1H), 2.28 (s, 3H); 13C NMR (126 MHz, CDCl3)
d 169.5,
150.4, 144.1, 141.1, 134.6, 131.1, 129.7, 129.5, 129.2, 128.0, 127.2, 126.0,
125.3, 121.6, 117.3, 58.6, 41.6, 34.8, 21.6. IR (KBr) 1755, 1722, 1384,
1168, 754; HRMS (ESI) calcd for C23H21NNaSO4 [MþNa]þ: 430.1084,
found 430.1087.
d
7.78 (d, J ¼ 8.2 Hz, 2H), 7.38 (t, J ¼ 7.9 Hz, 2H), 7.32 (d, J ¼ 8.1 Hz,
2H), 7.23 (dd, J ¼ 10.3, 4.6 Hz, 1H), 7.11 (d, J ¼ 7.7 Hz, 2H), 3.98 (m,
1H), 3.54 (dd, J ¼ 16.5, 4.3 Hz, 1H), 3.22 (p, J ¼ 11.0 Hz, 1H), 2.81 (dd,
J ¼ 16.5, 8.3 Hz, 1H), 2.42 (s, 3H), 2.01 (dd, J ¼ 12.7, 7.3 Hz, 1H),
1.61e1.52 (m, 1H), 1.42 (m, 2H), 1.36 (m, 2H), 1.32e1.15 (m, 3H),
1.15e1.02 (m, 1H), 0.77 (ddd, J ¼ 13.1, 9.4, 3.7 Hz, 1H), 0.65e0.55 (m,
4.1.18. Phenyl 2-(2-tosylisoindolin-1-yl)acetate (2r)
75.3 mg, 93% yield; White solid, m.p. ¼ 101e102 ꢁC; Rf ¼ 0.43
(petroleum ether/ethyl acetate 4:1). 1H NMR (500 MHz, CDCl3)
1H); 13C NMR (126 MHz, CDCl3)
d 170.2, 150.5, 143.6, 134.1, 129.7,
d
7.72 (d, J ¼ 8.1 Hz, 2H), 7.33e7.26 (m, 2H), 7.22e7.19 (m, 2H),
129.4, 127.6, 125.9, 121.6, 115.2, 55.9, 41.9, 41.2, 36.4, 33.9, 25.8, 23.6,
22.8, 21.6. IR (KBr) 1755, 1493, 1126, 75, 688; HRMS (ESI) calcd for
7.19e7.13 (m, 4H), 7.11e7.06 (m,1H), 6.98 (d, J ¼ 7.9 Hz, 2H), 5.32 (m,
1H), 4.71 (dd, J ¼ 13.8, 2.2 Hz, 1H), 4.51 (d, J ¼ 13.8 Hz, 1H), 3.44 (dd,
C
24H29NNaSO4 [MþNa]þ: 450.1710, found 450.1706.
J ¼ 16.6, 4.2 Hz, 1H), 3.13 (dd, J ¼ 16.6, 6.7 Hz, 1H), 2.30 (s, 3H); 13
C
NMR (126 MHz, CDCl3)
d 169.5, 150.6, 143.9, 139.2, 135.7, 134.0,
4.1.14. 2,4-dichlorophenyl 2-(2-tosyl-2-azaspiro[4.5]decan-3-yl)
acetate (2n)
129.9, 129.4, 128.3, 128.0, 127.6, 125.9, 122.7, 122.6, 121.6, 62.0, 53.9,
42.8, 21.5. IR (KBr) 1753, 1724, 1346, 1164, 754; HRMS (ESI) calcd for
C
23H21NNaSO4 [MþNa]þ: 430.1084, found 430.1086.
87.7 mg, 89% yield; Colorless oil; Rf ¼ 0.23 (petroleum ether/
ethyl acetate 4:1). 1H NMR (500 MHz, CDCl3)
d
7.77 (d, J ¼ 8.2 Hz,
2H), 7.46 (d, J ¼ 2.4 Hz, 1H), 7.35e7.29 (m, 2H), 7.26 (s, 1H), 7.16 (dd,
J ¼ 8.5, 4.5 Hz, 1H), 3.97 (m, 1H), 3.59 (dd, J ¼ 16.5, 4.3 Hz, 1H), 3.22
(q, J ¼ 10.9 Hz, 2H), 2.86 (dd, J ¼ 16.5, 8.2 Hz, 1H), 2.43 (s, 3H), 2.01
(dd, J ¼ 12.8, 7.3 Hz, 1H), 1.64e1.52 (m, 1H), 1.50e1.41 (m, 2H),
1.41e1.32 (m, 2H), 1.33e1.16 (m, 3H), 1.15e1.02 (m, 1H), 0.77 (ddd,
J ¼ 13.1, 9.3, 3.8 Hz, 1H), 0.66e0.54 (m, 1H); 13C NMR (126 MHz,
4.1.19. Phenyl 2-(1-tosylpiperidin-2-yl)acetate (4a)
61.1 mg, 82% yield; Colorless oil; Rf ¼ 0.23 (petroleum ether/
ethyl acetate 4:1). 1H NMR (500 MHz, CDCl3)
d
7.75 (d, J ¼ 8.2 Hz,
2H), 7.40e7.34 (m, 2H), 7.28 (d, J ¼ 8.0 Hz, 2H), 7.22 (dd, J ¼ 13.0,
5.6 Hz, 1H), 7.10e7.06 (m, 2H), 4.68 (m, 1H), 3.84 (dd, J ¼ 13.8,
4.0 Hz, 1H), 3.12e2.98 (m, 2H), 2.88e2.75 (m, 2H), 2.42 (s, 3H), 1.66
(d, J ¼ 5.3 Hz, 1H), 1.59 (m, 2H), 1.57 (m, 1H), 1.41e1.29 (m, 1H); 13
C
CDCl3)
d 169.1, 145.6, 143.7, 133.9, 132.0, 130.0, 129.6, 128.0, 127.7,
127.7, 124.8, 55.4, 41.6, 41.2, 36.3, 33.9, 25.8, 23.7, 22.8, 21.6. IR (KBr)
1767, 1474, 1160, 1095, 664; HRMS (ESI) calcd for C24H27NCl2NaSO4
[MþNa]þ: 518.0930, found 518.0927.
NMR (126 MHz, CDCl3)
d 169.3, 150.5, 143.2, 138.1, 129.8, 129.4,
127.1, 125.9, 121.8, 121.6, 49.8, 41.0, 35.4, 27.8, 24.5, 21.5, 18.4. IR
(KBr) 1755, 1493, 1338, 1193, 652; HRMS (ESI) calcd for
C
20H23NNaSO4 [MþNa]þ: 396.1240, found 396.1239.
4.1.15. Phenyl 2-((4R)-4-(((tert-butyldiphenylsilyl)oxy)methyl)-1-
((4-nitrophenyl)sulfonyl)pyrrolidin-2-yl)acetate (2o)
4.1.20. Phenyl 2-(3-methyl-1-tosylpiperidin-2-yl)acetate (4b)
60.0 mg, 78% yield, dr > 20:1; Colorless oil; Rf ¼ 0.33 (petroleum
69.0 mg, 54% yield; dr ¼ 3:1; White solid, m.p. ¼ 163e164 ꢁC;
Rf ¼ 0.23 (petroleum ether/ethyl acetate 8:1). 1H NMR (500 MHz,
ether/ethyl acetate 4:1). 1H NMR (400 MHz, CDCl3)
d 7.74 (d,
CDCl3)
d
8.26 (d, J ¼ 8.2 Hz, 2H), 8.07 (d, J ¼ 8.3 Hz, 2H), 7.48e7.29
J ¼ 8.2 Hz, 2H), 7.37 (t, J ¼ 7.9 Hz, 2H), 7.28 (d, J ¼ 8.1 Hz, 2H), 7.23 (t,
J ¼ 7.4 Hz, 1H), 7.11e7.04 (m, 2H), 4.71 (dd, J ¼ 13.2, 6.7 Hz, 1H), 3.87
(dd, J ¼ 14.0, 3.1 Hz,1H), 3.04 (td, J ¼ 13.8, 2.7 Hz,1H), 2.86e2.72 (m,
2H), 2.42 (s, 3H), 1.80e1.69 (m, 1H), 1.64 (dd, J ¼ 14.5, 12.9 Hz, 1H),
1.60e1.50 (m, 1H), 1.25e1.16 (m, 1H), 1.05e0.93 (m, 1H), 0.85 (d,
(m, 7H), 7.09 (dd, J ¼ 15.0, 7.9 Hz, 5H), 4.33 (d, J ¼ 24.6 Hz, 3H), 4.27
(m, 1H), 3.68e3.56 (m, 1H), 3.39 (dd, J ¼ 17.1, 4.7 Hz, 1H), 3.35 (d,
J ¼ 11.7 Hz, 1H), 2.79 (dd, J ¼ 16.8, 6.5 Hz, 1H), 2.06 (d, J ¼ 6.4 Hz,
1H), 1.78 (t, J ¼ 9.2 Hz, 1H), 0.84 (d, J ¼ 28.7 Hz, 9H); 13C NMR
(126 MHz, CDCl3)
d
169.9, 135.5, 135.4, 130.2, 129.5, 129.1, 127.9,
J ¼ 6.4 Hz, 3H); 13C NMR (101 MHz, CDCl3)
d 169.3, 150.5, 143.2,
124.4, 121.6, 70.4, 58.1, 55.5, 41.9, 40.7, 26.8, 26.6, 18.8. IR (KBr) 1748,
1646, 1350, 1164, 743; HRMS (ESI) calcd for C34H36N2NaSSiO7
[MþNa]þ: 667.1905, found 667.1900.
138.1, 129.7, 129.4, 127.1, 125.9, 121.5, 50.0, 40.9, 36.3, 35.9, 33.0,
24.9, 22.0, 21.5. IR (KBr) 1755, 1493, 1338, 1155, 697; HRMS (ESI)
calcd for C21H25NNaSO4 [MþNa]þ: 410.1397, found 410.1393.
6