Asymmetric Hydrogenation of Aromatic Carbocyclic Rings and Thiophenes

Zhi-Shi Ye; Lei Shi; Yong-Gui Zhou

doi:10.1055/s-0033-1341029

Synlett, Table of Contents

Synlett 2014; 25(07): 928-931
DOI: 10.1055/s-0033-1341029

new tools in synthesis

Asymmetric Hydrogenation of Aromatic Carbocyclic Rings and Thiophenes

Zhi-Shi Ye

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

,

Lei Shi*

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

^bState Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, P. R. of China, Fax: +86(411)84379220 Email: shileichem@dicp.ac.cn

,

Yong-Gui Zhou

^aDalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. of China

› Author Affiliations

Abstract

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Abstract

Recent advance on asymmetric hydrogenation of aromatic carbocyclic rings and thiophenes has been described with the chiral ruthenium catalyst. It represents a great breakthrough in the area of asymmetric hydrogenation as well as opens up a new pathway for the facile synthesis of valuable optically active carbocyclic rings and dihydro- and tetrahydrothiophenes.

Key words

asymmetric hydrogenation - naphthalenes - thiophenes - ruthenium - N-heterocyclic carbene

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References

References
1 Zhou Y.-G. Acc. Chem. Res. 2007; 40: 1357
2 Wang D.-S, Chen Q.-A, Lu S.-M, Zhou Y.-G. Chem. Rev. 2012; 112: 2557
3 Glorius F. Org. Biomol. Chem. 2005; 3: 4171
4 Kuwano R. Heterocycles 2008; 76: 909
5 Fleury-Brégeot N, de la Fuente V, Castillón S, Claver C. ChemCatChem 2010; 2: 1346
6 Wang L, He W, Yu Z. Chem. Soc. Rev. 2013; 42: 499
7 Rodriguez JA, Hrbek J. Acc. Chem. Res. 1999; 32: 719
8 Topsøe H, Clausen BS, Massoth FE. Hydrotreating Catalysis: Science and Technology . Springer; Berlin: 1996
9 Bianchini C, Meli A. Acc. Chem. Res. 1998; 31: 109
10 Urban S, Ortega N, Glorius F. Angew. Chem. Int. Ed. 2011; 50: 3803
11 Urban S, Beiring B, Ortega N, Paul D, Glorius F. J. Am. Chem. Soc. 2012; 134: 15241
12 Kuwano R, Morioka R, Kashiwabara M, Kameyama N. Angew. Chem. Int. Ed. 2012; 51: 4136
13 Borowski AF, Sabo-Etienne S, Donnadieu B, Chaudret B. Organometallics 2003; 22: 1630
14 Borowski AF, Vendier L, Sabo-Etienne S, Rozycka-Sokolowska E, Gaudynb AV. Dalton Trans. 2012; 41: 14117
15 N-Heterocyclic Carbenes in Synthesis . Nolan SP. Wiley-VCH; Weinheim: 2006
16 Glorius F. N-Heterocyclic Carbenes in Transition Metal Catalysis. Springer; Berlin: 2007
17 Diez-González S, Marion N, Nolan SP. Chem. Rev. 2009; 109: 3612
18 Vougioukalakis GC, Grubbs RH. Chem. Rev. 2010; 110: 1746
19 Kantchev EA. B, O’Brien CJ, Organ MG. Angew. Chem. Int. Ed. 2007; 46: 2768
20 Vora HU, Rovis T. Aldrichimica Acta 2011; 44: 3
21 Nair V, Menon RS, Biju AT, Sinu CR, Paul RR, Jose A, Sreekumar V. Chem. Soc. Rev. 2011; 40: 5336
22 Enders D, Niemeier O, Henseler A. Chem. Rev. 2007; 107: 5606
23 Phillips EM, Chan A, Scheidt KA. Aldrichimica Acta 2009; 42: 55
24 Kuwano R, Kaneda K, Ito T, Sato K, Kurokawa T, Ito Y. Org. Lett. 2004; 6: 2213
25 Dröge T, Glorius F. Angew. Chem Int. Ed. 2010; 49: 6940
26 Perrin L, Clot E, Eisenstein O, Loch J, Crabtree RH. Inorg. Chem. 2001; 40: 5806
27 Lever AB. P. Inorg. Chem. 1990; 29: 1271
28 Fielder SS, Osborne MC, Lever AB. P, Pietro WJ. J. Am. Chem. Soc. 1995; 117: 6990
29 Süßner M, Plenio H. Chem. Commun. 2005; 5417
30 Leuthäußer S, Schmidts V, Thiele CM, Plenio H. Chem. Eur. J. 2008; 14: 5465