Savitha Muramulla et al.
COMMUNICATIONS
directly transferred to a pre-packed silica gel column and
purified by column chromatography to furnish the desired
product 3a; yield: 22.9 mg (99%; 98% ee).
Chem. Eur. J. 2010, 16, 8480; h) W.-H. Wang, T. Abe, X.-
B. Wang, K. Kodama, T. Hirose, G.-Y. Zhang, Tetrahe-
dron: Asymmetry 2010, 21, 2925; i) A.-B. Xia, D.-Q. Xu,
S.-P. Luo, J.-R. Jiang, J. Tang, Y.-F. Wang, Z.-Y. Xu,
Chem. Eur. J. 2010, 16, 801; j) J. A. Fuentes, T. Lebl,
A. M. Z. Slawin, M. L. Clarke, Chem. Sci. 2011, 2, 1997.
[5] For examples, see: a) L.-Y. Wu, G. Bencivenni, M. Man-
cinelli, A. Mazzanti, G. Bartoli, P. Melchiorre, Angew.
Chem. 2009, 121, 7332; Angew. Chem. Int. Ed. 2009, 48,
7196; b) F. Yu, X. Sun, Z. Jin, S. Wen, X. Liang, J. Ye,
Chem. Commun. 2010, 46, 4589; c) F. Yu, Z. Jin, H.
Huang, T. Ye, X. Liang, J. Ye, Org. Biomol. Chem. 2010,
8, 4767; d) J.-F. Bai, L. Peng, L.-l. Wang, L.-X. Wang, X.-
Y. Xu, Tetrahedron 2010, 66, 8928; e) J. Wang, M.-M.
Zhang, S. Zhang, Z.-A. Xu, H. Li, X.-H. Yu, W. Wang,
Synlett 2011, 473; f) T. Miura, A. Masuda, M. Ina, K.
Nakashima, S. Nishida, N. Tada, A. Itoh, Tetrahedron:
Asymmetry 2011, 22, 1605; g) Z.-w. Ma, Y.-x. Liu, P.-l.
Li, H. Ren, Y. Zhu, J.-c. Tao, Tetrahedron: Asymmetry
2011, 22, 1740; h) F. Xue, L. Liu, S. Zhang, W. Duan, W.
Wang, Chem. Eur. J. 2010, 16, 7979; i) G.-L. Zhao, Y.
Xu, H. Sunden, L. Erikson, M. Sayah, A. Cordova,
Chem. Commun. 2007, 734; j) N. Mase, F. Tanaka, C. F.
Barbas III, Angew. Chem. 2004, 116, 2474; Angew.
Chem. Int. Ed. 2004, 43, 2420; k) T. C. Nugent, A. Sadiq,
A. Bibi, T. Heine, L. L. Zeonjuk, N. Vankova, B. S.
Bassil, Chem. Eur. J. 2012, 18, 4088.
[6] For related examples: a) Z. Jiang, W. Ye, Y. Yang, C.-H.
Tan, Adv. Synth. Catal. 2008, 350, 2345; b) S. Harada, N.
Kumagai, T. Kinoshita, S. Matsunaga, M. Shibasak, J.
Am. Chem. Soc. 2003, 125, 2582.
[7] For details, please see the Supporting Information.
[8] For a review, see: L.-W. Xu, Y. Lu, Org. Biomol. Chem.
2008, 6, 2047.
[9] CCDC 915320 contains the supplementary crystallo-
graphic data for compound 3e. These data can be ob-
tained free of charge from The Cambridge Crystallo-
quest/cif.
Acknowledgements
The generous financial support of this research from the Na-
tional Science Foundation (Grant No. CHE 0909954) and the
Welch Foundation (Grant No. AX-1593) is gratefully ac-
knowledged.
References
[1] M. L. Clarke, J. A. Fuentes, Angew. Chem. 2007, 119,
948; Angew. Chem. Int. Ed. 2007, 46, 930.
[2] a) T. Mandal, C.-G. Zhao, Angew. Chem. 2008, 120,
7828; Angew. Chem. Int. Ed. 2008, 47, 7714; b) S. Mura-
mulla, C.-G. Zhao, Tetrahedron Lett. 2011, 52, 3905;
c) D. Sinha, T. Mandal, G. Sanjib, J. J. Goldman, J. C.-G.
Zhao, Chin. J. Chem. 2012, 30, 2624; d) D. Sinha, S.
Perera, J. C.-G. Zhao, Chem. Eur. J., in press; DOI:
10.1002/ chem.201300168.
[3] For reviews on self-assembled organocatalysts, see: a) J.-
F. Briere, S. Oudeyer, V. Dalla, V. Levacher, Chem. Soc.
Rev. 2012, 41, 1696; b) J. Meeuwissen, J. N. H. Reek,
Nat. Chem. 2010, 2, 615; c) S. Piovesana, D. M. Scarpino
Schietroma, M. Bella, Angew. Chem. 2011, 123, 6340;
Angew. Chem. Int. Ed. 2011, 50, 6216.
[4] For examples, see: a) D. Q. Xu, H. D. Yue, S. P. Luo,
A. B. Xia, S. Zhang, Z. Y. Xu, Org. Biomol. Chem. 2008,
6, 2054; b) D. Uraguchi, Y. Ueki, T. Ooi, Science 2009,
326, 120; c) M. Bella, D. M. Scarpino Schietroma, P. P.
Cusella, T. Gasperi, V. Visca, Chem. Commun. 2009,
597; d) ꢂ. Reis, S. Eymur, B. Reis, A. S. Demir, Chem.
Commun. 2009, 1088; e) A. S. Demir, S. Eymur, Tetrahe-
dron: Asymmetry 2010, 21, 112; f) N. El-Hamdouni, X.
Companyꢃ, R. Rios, A. Moyano, Chem. Eur. J. 2010, 16,
1142; g) F. Rodrꢄguez-Llansola, J. F. Miravet, B. Escuder,
1264
ꢁ 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2013, 355, 1260 – 1264