COMMUNICATIONS
Lin Chen et al.
ether/EtOAc) to afford pure indoline 4b. The ee values were
determined by HPLC with chiral stationary phases.
(2R,3R)-3-(4-Chlorobenzyl)-2-methylindoline (4b): Ob-
2256; b) Z. Wang, X. Ye, S. Wei, P. Wu, A. Zhang, J.
Sun, Org. Lett. 2006, 8, 999–1001; c) Z. Y. Wang, M. N.
Cheng, P. C. Wu, S. Y. Wie, J. Sun, Org. Lett. 2006, 8,
3045–3048; d) A. V. Malkov, A. Liddon, P. Ramirez-
ACHTUNGTRENNUNG
tained as a yellow semi-solid after flash chromatography;
yield: 95%; the enantiomeric excess was determined to be
89% by HPLC analysis [Chiralpak OD-H column, 10% 2-
ˇ
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Lopez, L. Bendova, D. Haigh, P. Kocovsky, Angew.
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propanol/n-hexane, 1 mLminÀ1]:
tmajor =16.26 min, tminor =
ˇ
2006, 45, 1432–1435; e) A. V. Malkov, S. Stoncius, P.
9.77 min; [a]2D0: À70.3 (c 0.31 in CHCl3); 1H NMR
(300 MHz, CDCl3): d=1.27 (d, J=6.5 Hz, 3H), 2.79–2.86
(m, 1H), 2.93–3.00 (m, 1H), 3.43–3.51 (m, 2H), 3.99–4.06
ˇ
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Kocovsky, Angew. Chem. 2007, 119, 3796–3798; Angew.
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(m, 1H), 6.54–6.68 (m, 3H), 7.03–7.17ACTHNUTRGNE(NUG m, 3H), 7.29 (d, J=
8.3 Hz, 2H); 13C NMR (150 MHz, CDCl3): d=16.4, 33.8,
46.0, 58.5, 109.5, 118.4, 125.0, 127.7, 128.4, 130.6, 131.7,
131.8, 138.9, 150.5; ESI HR-MS: m/z=258.1056, calcd. for
C16H16ClN+H+: 258.1044.
ˇ
[6] For examples, see: a) A. V. Malkov, S. Stoncius, K.
Acknowledgements
ˇ
´
Vrankova, M. Arndt, P. Kocovsky, Chem. Eur. J. 2008,
14, 8082–8085; b) H. J. Zheng, W. B. Chen, Z. J. Wu,
J. G. Deng, W. Q. Lin, W. C. Yuan, X. M. Zhang, Chem.
Eur. J. 2008, 14, 9864–9867; c) X. Wu, Y. Li, C. Wang,
L. Zhou, X. Lu, J. Sun, Chem. Eur. J. 2011, 17, 2846–
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W.-C. Yuan, X.-M. Zhang, Angew. Chem. 2011, 123,
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Angew. Chem. 2011, 123, 10849–10852; Angew. Chem.
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We are grateful for financial supports from the National Nat-
ural Science Foundation of China (Project Nos. 21272227
and 91013006) and from Science and Technology Depart-
ment of Sichuan (Project No. 2012SZ0219).
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Adv. Synth. Catal. 2014, 356, 2224 – 2230