ChemComm
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COMMUNICATION
Journal Name
Scholarship Council graduate scholarship. We also thank Dr.
Claudia El-Nachef for helpful discussions.
Chem. Int. Ed., 2000, 39, 2281.
DOI: 10.1039/C7CC04950A
11 For selected reviews, see: a) Y.-M. Cui, Y. Lin and L.-W. Xu,
Coord. Chem. Rev., 2017, 330, 37; b) J. S. Harvey and V.
Gouverneur, Chem. Comm., 2010, 46, 7477; c) M. Dutartre, J.
Bayardon and S. Juge, Chem. Soc. Rev., 2016, 45, 5771; d) Y.
N. Ma, S. X. Li and S. D. Yang, Acc. Chem. Res., 2017, 50, 1480.
For selected examples, see: e) Y. Toda, M. Pink and J. N.
Johnston, J. Am. Chem. Soc., 2014, 136, 14734; f) Z. J. Du, J.
Guan, G. J. Wu, P. Xu, L. X. Gao and F. S. Han, J. Am. Chem.
Soc., 2015, 137, 632; g) Z. Q. Lin, W. Z. Wang, S. B. Yan and W.
L. Duan, Angew. Chem. Int. Ed., 2015, 54, 6265; h) L. Liu, A. A.
Zhang, Y. Wang, F. Zhang, Z. Zuo, W. X. Zhao, C. L. Feng and
W. Ma, Org. Lett., 2015, 17, 2046; i) R. Beaud, R. J. Phipps
and M. J. Gaunt, J. Am. Chem. Soc., 2016, 138, 13183; j) Z.
Huang, X. Huang, B. Li, C. Mou, S. Yang, B. A. Song and Y. R.
Chi, J. Am. Chem. Soc., 2016, 138, 7524; k) K. M. Lim and T.
Hayashi, J. Am. Chem. Soc., 139, 8122; l) Y. N. Ma, M. X.
Cheng and S. D. Yang, Org. Lett., 2017, 19, 600; m) Y. Sun and
N. Cramer, Angew. Chem. Int. Ed., 2017, 56, 364; n) Z. Lian, B.
N. Bhawal, P. Yu, B. Morandi, Science, 2017, 356, 1059. o) D.
A. DiRocco, Y. Ji, E. C. Sherer, A. Klapars, M. Reibarkh, J.
Dropinski, R. Mathew, P. Maligres, A. M. Hyde, J. Limanto, A.
Brunskill, R. T. Ruck, L.-C. Campeau and I. W. Davies, Science,
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Notes and references
1
For selected reviews on enamine and iminium catalysis, see:
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(i) Z. Shao and H. Zhang, Chem. Soc. Rev., 2009, 38, 2745.
For reviews, see: (a) R. Pascal, Eur. J. Org. Chem., 2003, 1813;
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(b) K. L. Tan, ACS Catal., 2011,
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5
Selected examples for nitrile hydration: (a) R. Pascal, J.
Taillades and A. Commeyras, Bull. Soc. Chim. Fr., II, 1978, 3–4
177; (b) R. Pascal, J. Taillades and A. Commeyras,
Tetrahedron, 1978, 34, 2275; (c) R. Pascal, J. Taillades and A.
Commeyras, Tetrahedron, 1980, 36, 2999; (d) R. Pascal, M. L.
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12 For selected reviews and examples, see: a) T. Lönnberg, M.
Ora and H. Lönnberg, Mini-Reviews in Organic Chemistry,
2010, 7, 33-43. b) A. Monroy-Noyola, B. Trujillo, P. Yescas, F.
US4243814, 1981. For efforts toward asymmetric variants; (e)
P.-H. Lagriffoul, Z. Tadros, J. Taillades and A. Commeyras, J.
Chem. Soc., Perkin Trans. 2, 1992, 1279. See also: (f) R. Sola, J.
Taillades, J. Brugidou and A. Commeyras, New J. Chem., 1989,
13, 881; (g) S. Chitale, J. S. Derasp, B. Hussain, K. Tanveer and
A. M. Beauchemin, Chem. Commun., 2016, 52, 13147-13150.
Selected examples for transesterification: (h) T. Sammakia
and T. B. Hurley, J. Am. Chem. Soc., 1996, 118, 8967; (i) T.
Sammakia and T. B. Hurley, J. Org. Chem., 1999, 64, 4652; (j)
T. Sammakia and T. B. Hurley, J. Org. Chem., 2000, 65, 974.
(a) B. Xu, L.-L. Shi, Y.-Z. Zhang, Z.-J. Wu, L.-N. Fu, C.-Q. Luo, L.-
Martínez-Salazar, S. García-Jiménez, C. Ríos and E. Vilanova,
Arch. Toxicol., 2015, 89, 1801. c) H. Wang, L. Su, R. Li, S.
Zhang, J. Fan, F. Zhang, T. P. Nguyen and K. L. Wooley, ACS
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Froeyen, P. Herdewijn, M. Tho Nguyen and A. Ceulemans,
Phys. Chem. Chem. Phys., 2009, 11, 7274. Also see refs 14-19.
13 P. G. M. Wuts. Greene’s Protective Groups in Organic
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14 A. W. Garrison and C. E. Boozer, J. Am. Chem. Soc., 1968, 90
,
3486.
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,
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(a) Y. Wu, Y.-Q. Chen, T. Liu, M. D. Eastgate and J.-Q. Yu, J.
Am. Chem. Soc., 2016, 138, 14554; (b) Y. Liu and H. Ge, Nat.
16 T. Koizumi and P. Haake, J. Am. Chem. Soc., 1973, 95, 8073.
17 H. M. I. Osborn, J. B. Sweeney and B. Howson, Synlett, 1994,
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18 (a) S. Kingsley, A. Vij and V. Chandrasekhar, Inorg. Chem.,
2001, 40, 6057-6060; (b) P. Malik, D. Chakraborty and V.
Ramkumar, Polyhedron, 2010, 29, 2142.
Chem, 2017,
9, 26; (c) A. Yada, W. Liao, Y. Sato and M.
Murakami, Angew. Chem. Int. Ed., 2017, 56, 1073.
(a) C. R. Hesp, M. J. MacDonald, M. M. Zahedi, D. A. Bilodeau,
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(c) N. Guimond, M. J. MacDonald, V. Lemieux and A. M.
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19 T. Murai, T. Takenaka, S. Inaji and Y. Tonomura, Chem. Lett.,
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20 P. Schmidt, C. Stress and D. Gillingham, Chem. Sci., 2015, 6,
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21 P. Schmidt, L. Zhou, K. Tishinov, K. Zimmermann and D.
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22 W. P. Jencks, J. Am. Chem. Soc., 1959, 81, 475.
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W. P. Jencks and M. Gilchrist, J. Am. Chem. Soc., 1964, 86,
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For other examples of aldehyde catalysis in prebiotic
chemistry, see: (a) J. Taillades, I. Beuzelin, L. Garrel, V.
Tabacik, C. Bied and A. Commeyras, Origins Life Evol.
Biospheres, 1998, 28, 61; (b) see reference 2a; (c) see
reference 3g; (d) A. J. Wagner, D. Y. Zubarev, A. Aspuru-Guzik
and D. G. Blackmond, ACS Central Sci., 2017, 3, 322.
4 | J. Name., 2015, 00, 1-3
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