Mendeleev Commun., 2015, 25, 168–170
6 (a) V. Srivastava, J. Chem. Sci., 2013, 125, 1523; (b) A. Bañón-Caballero,
aldol reactions in ketone–ketone systems to afford corresponding
aldols in high yields and with moderate to high enantioselectivity.
Catalyst 2a can be recycled five times, though with a decrease
in conversion and ee values of the product. The erosion of enantio-
selectivity was attributed to a gradual off-cycle epimerization of
the catalyst during the catalytic process.
G. Guillena, C. Nájera, E. Faggi, R. M. Sebastián and A. Vallribera,
Tetrahedron, 2013, 69, 1307; (c) R. Pedrosa, J. M. Andrés, R. Manzano
and C. Pérez-López, Tetrahedron Lett., 2013, 54, 3001.
(a) C. H. Senanayake, K. Fang, P. Grover, R. P. Bakale, C. P. Vanden-
bossche and S. A. Wald, Tetrahedron Lett., 1999, 40, 819; (b) P. T. Grover,
N. N. Bhongle, S. A. Wald and C. H. Senanayake, J. Org. Chem., 2000,
7
6
5, 6283; (c) S. Masumoto, M. Suzuki, M. Kanai and M. Shibasaki,
Tetrahedron Lett., 2002, 43, 8647; (d) P. Gupta, R. A. Fernandes and
P. Kumar, Tetrahedron Lett., 2003, 44, 4231; (e) S. Masumoto, M. Suzuki,
M. Kanai and M. Shibasaki, Tetrahedron, 2004, 60, 10497; (f) O. Tokuda,
T. Kano, W. G. Gao, I. Ikemolo and K. Maruoka, Org. Lett., 2005, 7,
This work was supported by the Russian Foundation for Basic
Research (grant nos. 12-03-00420 and 14-03-31321).
Online Supplementary Materials
5
103.
Supplementary data associated with this article can be found
in the online version at doi:10.1016/j.mencom.2015.05.002.
8
(a) F. Wang, Y. Xiong, X. Liu and X. Feng, Adv. Synth. Catal., 2007,
349, 2665; (b) J. Liu, Z.-G.Yang, Z.Wang, F.Wang, X.-H. Chen, X.-H. Liu,
X.-M. Feng, Z.-S. Su and C.-W. Hu, J. Am. Chem. Soc., 2008, 130,
5
654; (c) Q.-Z. Liu, X.-L. Wang, S.-W. Luo, B.-L. Zheng and D.-B. Qin,
References
Tetrahedron Lett., 2008, 49, 7434; (d) M. Raj, G. S. Parashari and
V. K. Singh, Adv. Synth. Catal., 2009, 351, 1284; (e) Z. Jiang andY. Lu,
Tetrahedron Lett., 2010, 51, 1884; (f) X. Zhu, A. Lin, L. Fang, W. Li,
Ch. Zhu andY. Cheng, Chem. Eur. J., 2011, 17, 8281; (g) S. F. Viózquez,
A. Bañón-Caballero, G. Guillena, C. Nájera and E. Gómez-Bengoa, Org.
Biomol. Chem., 2012, 10, 4029.
(a) K. Mikami,Y. Kawakami, K. Akiyama and K. Aikawa, J. Am. Chem.
Soc., 2007, 129, 12950; (b) Zh. Tang, L.-F. Cun, X. Cui, A.-Q. Mi,
Y.-Zh. Jiang and L.-Z. Gong, Org. Lett., 2006, 8, 1263; (c) J. Liu, Z.Yang,
Zh. Wang, F. Wang, X. Chen, X. Liu, X. Feng, Zh. Su and Ch. Hu, J. Am.
Chem. Soc., 2008, 130, 5654; (d) C. G. Kokotos, J. Org. Chem., 2012,
1
(a) Science of Synthesis: Asymmetric Organocatalysis, eds. B. List and
K. Maruoka, Thieme, Stuttgart, 2012; (b) Comprehensive Enantio-
selective Organocatalysis: Catalysts, Reactions, and Applications,
ed. P. I. Dalco, Wiley-VCH, Weinheim, 2013.
2
(a) E. Marqués-López, R. P. Herrera and M. Christmann, Nat. Prod. Rep.,
2
010, 27, 1138; (b) P. Melchiorre, M. Marigo, A. Carlone and G. Bartoli,
9
Angew. Chem. Int. Ed., 2008, 47, 6138; (c) M. Rueping, J. Dufour and
F. R. Schoepke, Green Chem., 2011, 13, 1084.
3
4
(a) T. E. Kristensen and T. Hansen, Eur. J. Org. Chem., 2010, 3179;
(
b) U. Scheffler and R. Mahrwald, Synlett, 2011, 1660.
(a) D. E. Siyutkin, A. S. Kucherenko and S. G. Zlotin, in Comprehensive
Enantioselective Organocatalysis: Catalysts, Reactions, and Applications,
ed. P. I. Dalco, Wiley-VCH, Weinheim, 2013, p. 617; (b) B. Ni and
A. D. Headley, Chem. Eur. J., 2010, 16, 4426; (c) A. S. Kucherenko, D. E.
Siyutkin, O. V. Maltsev, S. V. Kochetkov and S. G. Zlotin, Russ. Chem.
Bull., Int. Ed., 2012, 61, 1313 (Izv. Akad. Nauk, Ser. Khim., 2012, 1299);
7
7, 1131.
1
1
0 X.-Y. Xu, Zh. Tang,Y.-Zh. Wang, Sh.-W. Luo, L.-F. Cun and L.-Zh. Gong,
J. Org. Chem., 2007, 72, 9905.
1 (a) P. Kirsch, Modern Fluoroorganic Chemistry, Wiley-VCH, Weinheim,
2
004; (b) R. D. Chambers, Fluorine in Organic Chemistry, Blackwell,
Oxford, 2004; (c) K. M. Muller, C. Faeh and F. Diederich, Science,
007, 317, 1881; (d) K. L. Kirk, Org. Proc. Res. Dev., 2008, 12, 305;
e) J. L. Aceña, A. E. Sorochinsky and V. A. Soloshonok, Synthesis,
012, 44, 1591.
(
(
d) R. Sebesta, I. Kmentova and S. Toma, Green Chem., 2008, 10, 484;
e) M. Lombardo and C. Trombini, ChemCatChem, 2010, 2, 135; (f) H. L.
2
(
2
Brozinski, J. P. Delaney and L. C. Henderson, Aust. J. Chem., 2013, 66,
44.
(a) W. Miao and T. H. Chan, Adv. Synth. Catal., 2006, 348, 1711;
b) M. Gruttadauria, F. Giacalone and R. Noto, Chem. Soc. Rev., 2008,
7, 1666; (c) D. E. Siyutkin, A. S. Kucherenko, M. I. Struchkova and
8
1
2 M. Lombardo, S. Easwar, F. Pasi, C. Trombini and D. D. Dhavale,
Tetrahedron, 2008, 64, 9203.
5
(
3
S. G. Zlotin, Tetrahedron Lett., 2008, 49, 1212; (d) A. F. Trindade,
P. M. P. Gois and C. A. M. Afonso, Chem. Rev., 2009, 109, 418;
(
e) D. E. Siyutkin, A. S. Kucherenko and S. G. Zlotin, Tetrahedron, 2010,
6
6, 513; (f) N. A. Larionova, A. S. Kucherenko, D. E. Siyutkin and S. G.
Zlotin, Tetrahedron, 2011, 67, 1948; (g) Y. Qiao and A. D. Headley,
Catalysts, 2013, 3, 7095.
Received: 5th December 2014; Com. 14/4521
–
170 –