Chemistry - A European Journal
10.1002/chem.202002811
FULL PAPER
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corresponding product. Conversions were determined by
H
NMR
A. Pfaltz, Angew. Chem. Int. Ed. 2013, 52, 7422-7425; c) Y. Zhu, K.
Burgess, Acc. Chem. Res. 2012, 45, 1623-1636; d) D. Zhao, L.
Candish, D. Paul, F. Glorius, ACS Catal. 2016, 6, 5978-5988.
spectroscopy and the ee values were determined by GC or SFC analysis
using chiral stationary phase. The configuration of the products was
determined by comparing their sign of optical rotation with literature data.
[10] a) T. Focken, G. Raabe, C. Bolm, Tetrahedron: Asymmetry 2004, 15,
1
1
693-1706; b) S. Nanchen, A. Pfaltz, Helv. Chim. Acta 2006, 89, 1559-
573; c) J. Passays, T. Ayad, V. Ratovelomanana-Vidal, A-C. Gaumont,
P. Jubault, E. Leclerc, Tetrahedron: Asymmetry 2011, 22, 562-574; d)
P. Gu, J. Zhang, Q. Xu, M. Shi, Dalton Trans. 2013, 42, 13599-13606.
11] a) K. Yoshida, T. Kamimura, H. Kuwabara, A. Tanagisawa, Chem
Commun. 2015, 51, 15442-15445; b) B. Ramasamy, M. K. Gangwar, P.
Ghosh, Eur. J. Inorg. Chem. 2017, 3253-3268.
Acknowledgements
[
The Swedish Research Council (VR), Stiftelsen Olle Engkvist
Byggmästare, The Swedish Energy Agency, SYNFLOW (FP7)
and the Knut and Alice Wallenberg foundation (KAW 2016:0072
[
[
12] M. V. Jiménez, J. Fernández-Tornos, F. J. Modrego, J. J. Pérez-
Torrente, L. A. Oro, Chem. Eur. J. 2015, 21, 17877-17889.
&
2018:0066) supported this work. J.J. thanks the Chulabhorn
13] Evaluated heteroaromatic substrates include 2-acetylpyridine, 3-
acetylpyridine, 4-acetylpyridine, 2-acetylfuran and 2-acetylthiophene.
Graduate Institute, Chulabhorn Royal Academy, Thailand for an
exchange scholarship to Stockholm University. The authors
thank Dr. T. Singh, Dr. B. Peters and Dr. J. Zheng for useful
discussions, Dr. X. Sheng for help with the kinetic study and Dr.
C. Margarita for proofreading the manuscript.
Keywords: ligand development • asymmetric hydrogenation • N-
heterocyclic carbene • iridium catalysis • ketones
[
1]
a) K. C. Nicolaou, S. A. Snyder in Classics in Total Synthesis II: More
Targets, Strategies, Methods, Wiley-VCH, Weinheim, 2003; b) J. J. Li,
E. J. Corey in Total Synthesis of Natural Products: At the Frontiers of
Organic Chemistry, Springer, Heidelberg, 2012; c) B-F. Sun,
Tetrahedron Lett. 2015, 56, 2133-2140; d) Z. G. Brill, M. L. Condakes,
C. P. Ting, T. J. Maimone, Chem. Rev. 2017, 117, 11753-11795; e) K.
Zheng, R. Hong, Nat. Prod. Rep. 2019, 36, 1546-1575.
[
[
2]
3]
a) T. Ohkuma, H. Ooka, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am.
Chem. Soc. 1995, 117, 2675-2676; b) S. Hashiguchi, A. Fujii, J.
Takehara, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1995, 117, 7562-
7
563; c) T. Ohkuma, H. Ooka, T. Ikariya, R. Noyori, J. Am. Chem. Soc.
995, 117, 10417-10418.
1
a) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97-102; b) J. S.
M. Samec, J-E. Bäckvall, P. G. Andersson, P. Brandt, Chem. Soc. Rev.
2
006, 35, 237-248; c) T. Ohkuma, N. Utsumi, K. Tsutsumi, K. Murata, C.
Sandoval, R. Noyori, J. Am. Chem. Soc. 2006, 128, 8724-8725; d) D.
Wang, D. Astruc, Chem. Rev. 2015, 115, 6621-6686.
[
[
4]
5]
a) K. Murata, T. Ikariya, R. Noyori, J. Org. Chem. 1999, 64, 2186-2187;
b) R. Malacea, R. Poli, E. Manoury, Coord. Chem. Rev. 2010, 254,
7
29-752; c) A. Bartoszewicz, N. Ahlsten, B. Martín-Matute, Chem. Eur.
J. 2013, 19, 7274-7302.
a) T. Ohkuma, M. Koizumi, K. Muñiz, G. Hilt, C. Kabuto, R. Noyori, J.
Am. Chem. Soc. 2002, 124, 6508-6509; b) Z-R. Dong, Y-Y. Li, J-S.
Chen, B-Z. Li, Y. Xing, J-X. Gao, Org. Lett. 2005, 7, 1043-1045; c) T.
Ohkuma, N. Utsumi, M. Watanabe, K. Tsutsumi, N. Arai, K. Murata,
Org. Lett. 2007, 9, 2565-2567; d) K. Eceraere, J-L. Scheffler, A.
Mortreux, J-F. Carpentier, Tetrahedron Lett. 2001, 42, 1899-1901; e) L.
De Luca, A. Mezzetti, Angew. Chem. Int. Ed. 2017, 56, 11949-11953.
a) L. Benhamou, E. Chardon, G. Lavigne, S. Bellemin-Laponnaz, V.
César, Chem. Rev. 2011, 111, 2705-2733; b) S. Díez-González, N.
Marion, S. P. Nolan, Chem. Rev. 2009, 109, 3612-3676.
[
[
6]
7]
a) H. Jacobsen, A. Correa, A. Poater, C. Costabile, L. Cavallo, Coord.
Chem. Rev. 2009, 253, 687-703; b) S. Díez-González, S. P. Nolan,
Coord. Chem. Rev. 2007, 251, 874-883; c) R. H. Crabtree, J.
Organomet. Chem. 2005, 690, 5451-5457; d) H. V. Huynh, Chem. Rev.
2
018, 118, 9457-9492.
[
8]
a) M. Poyatos, J. A. Mata, E. Peris, Chem. Rev. 2009, 109, 3677-3707;
b) P. de Frémont, N. Marion, S. P. Nolan, Coord. Chem. Rev. 2009,
2
53, 862-892; c) M. Iglesias, L. A. Oro, Chem. Soc. Rev. 2018, 47,
2
772-2808; d) S. Takaoka, A. Eizawa, S. Kusumoto, K. Nakajima, Y.
Nishibayashi, K. Nozaki, Organometallics 2018, 37, 3001-3009; e) C.
Friedel, A. Labande, E. Manoury, R. Poli, Coord. Chem. Rev. 2019, 394,
6
5-103.
[
9]
a) M. T. Powell, D-R. Hou, M. C. Perry, X. Cui, K. Burgess, J. Am.
Chem. Soc. 2011, 123, 8878-8879; b) A. Schumacher, M. Bernasconi,
5
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