Paper
Organic & Biomolecular Chemistry
5
3
.75–5.77 (m, 1H), 5.44–5.51 (m, 1H), 3.74–3.80 (m, 1H),
.47–3.62 (m, 4H), 3.27–3.30 (m, 1H), 1.42–1.49 (m, 4H), 0.75
Int. Ed., 2007, 46, 8748; (f) R. M. Williams and R. J. Cox,
Acc. Chem. Res., 2003, 36, 127.
1
3
(t, J = 7 Hz, 6H); C NMR (75 MHz, DMSO) δ (ppm): 176.8,
2 Selected reviews: (a) F. Zhou, Y.-L. Liu and J. Zhou, Adv.
Synth. Catal., 2010, 352, 1381; (b) R. Dalpozzo, G. Bartoli
and G. Bencivenni, Chem. Soc. Rev., 2012, 41, 7247;
(c) J. Yu, F. Shi and L.-Z. Gong, Acc. Chem. Res., 2011, 44,
1156; (d) W. He, L. Xie, Y. Xu, J. Xiang and L. Zhang, Org.
Biomol. Chem., 2012, 10, 3168; (e) D. Cheng, Y. Ishihara,
B. Tan and C. F. Barbas III, ACS Catal, 2014, 4, 743;
(f) A. Moyano and R. Rios, Chem. Rev., 2011, 111, 4703;
(g) R. Rios, Chem. Soc. Rev., 2012, 41, 1060; (h) N. R. Ball-
Jones, J. J. Badillo and A. K. Franz, Org. Biomol. Chem.,
2012, 10, 5165.
1
1
2
72.1, 145.8, 144.2, 134.5, 133.9, 127.1, 125.9, 123.8, 122.9,
22.3, 121.5, 109.4, 108.8, 76.0, 63.0, 58.1, 41.3, 40.8, 33.4,
0.3, 20.2, 11.1, 11.0. HRMS-ESI (m/z): Calcd for
+
C
24
H
24Cl
2
N
2
O
3
S, [M + H] : 491.09571, found: 491.09657.
(3S,4S,5R)-1′-Propyl-6′-chloro-spiro[4.3′]oxindole-spiro[5.3″]-
1
3
0
″-propyl-6″-chloro-oxindole-tetrahydrothiophen-3-ol
(ent-
2
5
p). White solid, mp: 167–168 °C; 82% yield, [α]
D
= −79.9 (c =
.36, CHCl ); (dr > 20 : 1, 82% ee). HPLC conditions: ee was
3
determined by HPLC analysis (Chiralcel OD-H, hexane/i-PrOH
−
1
=
8
90/10, 1.0 mL min , 254 nm). Retention time: tminor
.57 min, tmajor = 12.23 min.
=
3 Selected examples: (a) Q. Chen, J. Liang, S. Wang, D. Wang
and R. Wang, Chem. Commun., 2013, 49, 1657; (b) L. Tian,
X.-Q. Hu, Y.-H. Li and P.-F. Xu, Chem. Commun., 2013, 49,
7213; (c) X.-H. Chen, Q. Wei, S.-W. Luo, H. Xiao and
L.-Z. Gong, J. Am. Chem. Soc., 2009, 131, 13819; (d) K. Jiang,
Z.-J. Jia, S. Chen, L. Wu and Y.-C. Chen, Chem. – Eur. J.,
2010, 16, 2852; (e) G. Wang, X.-H. Liu, T.-Y. Huang,
Y.-L. Kuang, L.-L. Lin and X.-M. Feng, Org. Lett., 2012, 15,
76; (f) W.-B. Chen, Z.-J. Wu, Q.-L. Pei, L.-F. Cun,
X.-M. Zhang and W.-C. Yuan, Org. Lett., 2010, 12, 3132;
(g) H.-B. Yang and M. Shi, Org. Biomol. Chem., 2012, 10,
8236; (h) C. Cassani, X. Tian, E. C. Escudero-Adan and
P. Melchiorre, Chem. Commun., 2011, 47, 233; (i) S. Duce,
F. Pesciaioli, L. Gramigna, L. Bernardi, A. Mazzanti,
A. Ricci, G. Bartoli and G. Bencivenni, Adv. Synth. Catal.,
2011, 353, 860; ( j) X.-W. Dou and Y.-X. Lu, Chem. – Eur. J.,
2012, 18, 8315; (k) H.-M. Zhang, Z.-H. Gao and S. Ye, Org.
Lett., 2014, 16, 3079; (l) X. Companyó, A. Zea, A.-N. R. Alba,
A. Mazzanti, A. Moyano and R. Rios, Chem. Commun., 2010,
46, 6953; (m) G. Bencivenni, L.-Y. Wu, A. Mazzanti,
B. Giannichi, F. Pesciaioli, M.-P. Song, G. Bartoli and
P. Melchiorre, Angew. Chem., Int. Ed., 2009, 48, 7200.
1
′-Methyl-spiro[4.3′]oxindole-spiro[5.3″]1″-methyl-oxindole-
tetrahydrothiophen-3-one (5). White solid, mp: 163–164 °C;
9% yield, H NMR (300 MHz, CDCl ) δ (ppm): 7.42 (d, J =
Hz, 1H), 7.20–7.26 (m, 3H), 6.97–7.00 (m, 2H), 6.64 (d, J =
Hz, 1H), 4.01–4.24 (m, 2H), 3.14 (s, 3H), 3.12 (s, 3H);
NMR (75 MHz, CDCl ) δ (ppm): 202.8, 176.6, 168.9, 144.4,
43.8, 130.4, 129.9, 126.4, 125.2, 123.3, 123.3, 123.2, 122.9,
08.6, 108.3, 72.1, 58.2, 38.8, 26.4, 26.2. HRMS-ESI (m/z): Calcd
for C H N O S, [M + H] : 365.09544, found: 365.09604.
1
8
8
8
3
1
3
C
3
1
1
+
2
0
16 2 3
1
′-Octyl-spiro[4.3′]oxindole-spiro[5.3″]1″-octyl-oxindole-
3
1
(
7
-hydroxy-tetrahydrothiophen1,1-dioxide (6). White solid, mp:
90–191 °C; Quant. H NMR (300 MHz, CDCl ) δ (ppm): 7.55
d, J = 7 Hz, 1H), 7.43 (d, J = 7 Hz, 1H), 7.23–7.26 (m, 1H),
.19–7.23 (m, 1H), 6.96–7.00 (m, 1H), 6.91–6.96 (m, 1H), 6.67
t, J = 8 Hz, 2H), 5.64–5.66 (m, 1H), 4.33–4.38 (m, 1H),
.10–4.17 (m, 1H), 3.67–3.75 (m, 2H), 3.50–3.58 (m, 2H),
.29–2.39 (bs, 1H), 1.54–1.58 (m, 4H), 1.24–1.28 (m, 20H),
.86–0.94 (m, 6H); C NMR (75 MHz, CDCl ) δ (ppm): 173.0,
72.1, 144.6, 143.9, 130.5, 129.5, 128.3, 124.9, 124.5, 123.1,
22.6, 118.8, 108.6, 108.6, 74.4, 62.8, 58.5, 40.3, 31.8, 29.2,
1
3
(
4
2
0
1
1
2
1
3
3
9.2, 29.1, 29.1, 27.4, 27.3, 26.9, 26.8, 22.6, 14.1. HRMS-ESI
m/z): Calcd for C34
95.31809.
+
(
5
H
46
N
2
O
5
S, [M + H] : 595.32002, found:
4 Selected examples: (a) P. Prasanna, K. Balamurugan,
S. Perumal, P. Yogeeswari and D. Sriram, Eur. J. Med.
Chem., 2010, 45, 5653; (b) Y. Kia, H. Osman, R. S. Kumar,
V. Murugaiyah, A. Basiri, S. Perumal, H. A. Wahab and
C. S. Bing, Bioorg. Med. Chem. Lett., 2013, 21, 1696;
Acknowledgements
(
c) C. J. O’Connor, H. S. G. Beckmann and D. R. Spring,
We acknowledge the financial support for this study from the
National Natural Science Foundation of China (no. 21272230).
Chem. Soc. Rev., 2012, 41, 4444; (d) S. Dandapani and
L. A. Marcaurelle, Curr. Opin. Chem. Biol., 2010, 14, 362;
(
e) W. R. J. D. Galloway, A. Bender, M. Welch and
D. R. Spring, Chem. Commun., 2009, 2446; (f) J. E. Biggs-
Houck, A. Younai and J. T. Shaw, Curr. Opin. Chem. Biol.,
References
2010, 14, 371.
1
Selected examples: (a) K. Ding, Y. Lu, Z. N. Coleska,
G. Wang, S. Qiu, S. Shangary, W. Gao, D. Qin, J. Stuckey
and K. Krajewski, J. Med. Chem., 2006, 49, 3432;
5 Selected examples: (a) B. Tan, N. R. Candeias and
C. F. Barbas III, Nat. Chem., 2011, 3, 473; (b) W.-S. Sun,
G.-M. Zhu, C.-Y. Wu, L. Hong and R. Wang, Chem. – Eur. J.,
2012, 18, 6737; (c) F. Tan, H.-G. Cheng, B. Feng, Y.-Q. Zou,
S.-W. Duan, J.-R. Chen and W.-J. Xiao, Eur. J. Org. Chem.,
2013, 2071; (d) Y.-Y. Han, W.-B. Chen, W.-Y. Han, Z.-J. Wu,
X.-M. Zhang and W.-C. Yuan, Org. Lett., 2012, 14, 490;
(e) Y.-M. Cao, F.-F. Shen, F.-T. Zhang and R. Wang, Chem. –
Eur. J., 2013, 19, 1184; (f) W.-S. Sun, L. Hong, G.-M. Zhu,
(
b) S. Edmondson, S. J. Danishefsky, L. S. Lorenzino and
N. Rosen, J. Am. Chem. Soc., 1999, 121, 2147;
c) P. R. Sebahar and R. M. Williams, J. Am. Chem. Soc.,
000, 122, 5666; (d) J. Yang, X. Z. Wearing, P. W. L. Quesne,
J. R. Deschamps and J. M. Cook, J. Nat. Prod., 2008, 71,
431; (e) C. V. Galliford and K. A. Scheidt, Angew. Chem.,
(
2
1
Org. Biomol. Chem.
This journal is © The Royal Society of Chemistry 2015