Synthesis of Electronically
Deficient Atropisomeric Bisphosphine Ligands and Their Application
in Asymmetric Hydrogenation of Quinolines

De-Yang Zhang; Duo-Sheng Wang; Min-Can Wang; Chang-Bin Yu; Kai Gao; Yong-Gui Zhou

doi:10.1055/s-0030-1260129

PAPER

Synthesis of Electronically Deficient Atropisomeric Bisphosphine Ligands and Their Application in Asymmetric Hydrogenation of Quinolines

De-Yang Zhang^a,b, Duo-Sheng Wang^b, Min-Can Wang*^a, Chang-Bin Yu^b, Kai Gao^b, Yong-Gui Zhou*^b
^a Department of Chemistry, Zhengzhou University, Zhengzhou, Henan 450052, P. R. of China
Fax: +86(371)67769024; e-Mail: wangmincan@zzu.edu.cn;
^b State Key Laboratory of Catalysis, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, 457 Zhongshan Road, Dalian 116023, P. R. of China
Fax: +86(411)84379220; e-Mail: ygzhou@dicp.ac.cn;

Abstract

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Abstract

A series of electronically deficient atropisomeric bisphosphine ligands have been synthesized from (S)-MeO-BiPhep. The introduction of electron-withdrawing groups in the ligands had a dramatic influence on both the enantioselectivity and the activity of catalyst. The iridium complex of the MeO-BiPhep-based ligand bearing a trifluoromethanesulfonyl group was successfully applied in the asymmetric hydrogenation of quinolines with ee values of up to 95% and turnover numbers (TON) of up to 14,600.

Key words

iridium - asymmetric hydrogenation - electron-deficient ligands - quinolines

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References

1a Keay JG. In Comprehensive Organic Synthesis Vol. 8: Pergamon; Oxford: 1991. p.579

1b Katrizky AR. Rachwal S. Bachwal B. Tetrahedron 1996, 52: 15031

1c Barton DH. Nakanishi K. Meth-Cohn O. In Comprehensive Natural Products Chemistry Vol. 1-9: Elsevier; Oxford: 1999.

2 Wang W.-B. Lu S.-M. Yang P.-Y. Han X.-W. Zhou Y.-G. J. Am. Chem. Soc. 2003, 125: 10536

For recent reviews on hydrogenation of heteroaromatic compounds, see:

3a Dyson PJ. Dalton Trans. 2003, 2964

3b Glorius F. Org. Biomol. Chem. 2005, 3: 4171

3c Lu S.-M. Han X.-W. Zhou Y.-G. Chin. J. Org. Chem. 2005, 25: 634

3d Zhou Y.-G. Acc. Chem. Res. 2007, 40: 1357

3e Kuwano R. Heterocycles 2008, 76: 909

For our group’s work on the asymmetric hydrogenation of quinolines, see:

4a Lu S.-M. Han X.-W. Zhou Y.-G. Adv. Synth. Catal. 2004, 346: 909

4b Yang P.-Y. Zhou Y.-G. Tetrahedron: Asymmetry 2004, 15: 1145

4c Zhao Y.-J. Wang Y.-Q. Zhou Y.-G. Chin. J. Catal. 2005, 26: 737

4d Lu S.-M. Wang Y.-Q. Han X.-W. Zhou Y.-G. Angew. Chem. Int. Ed. 2006, 45: 2260

4e Wang D.-W. Zeng W. Zhou Y.-G. Tetrahedron: Asymmetry 2007, 18: 1103

4f Wang X.-B. Zhou Y.-G. J. Org. Chem. 2008, 73: 5640

4g Wang D.-W. Wang X.-B. Wang D.-S. Lu S.-M. Zhou Y.-G. Li Y.-X. J. Org. Chem. 2009, 74: 2780

4h Wang D.-W. Wang D.-S. Chen Q.-A. Zhou Y.-G. Chem. Eur. J. 2010, 16: 1133

4i Wang D.-S. Zhou Y.-G. Tetrahedron Lett. 2010, 51: 3014

For other groups’ work on metal-catalyzed asymmetric hydrogenation of quinolines, see:

5a Fache F. Synlett 2004, 2827

5b Fujita K.-I. Kitatsuji C. Furukawa S. Yamaguchi R. Tetrahedron Lett. 2004, 45: 3215

5c Xu L.-J. Lam K.-H. Ji J.-X. Wu J. Fan Q.-H. Lo W.-H. Chan ASC. Chem. Commun. 2005, 1390

5d Lam K.-H. Xu L.-J. Feng L.-C. Fan Q.-H. Lam F.-L. Lo W.-H. Chan ASC. Adv. Synth. Catal. 2005, 347: 1755

5e Wu J. Chan ASC. Acc. Chem. Res. 2006, 39: 711

5f Reetz MT. Li X.-G. Chem. Commun. 2006, 2159

5g Qiu L. Kwong FY. Wu J. Lam WH. Chan S. Yu W.-Y. Li Y.-M. Guo R. Zhou Z. Chan ASC. J. Am. Chem. Soc. 2006, 128: 5955

5h Yamagata T. Tadaoka H. Nagata M. Hirao T. Kataoka Y. Ratovelomanana-Vidal V. Genet JP. Mashima K. Organometallics 2006, 25: 2505

5i Chan S.-H. Lam K.-H. Li Y.-M. Xu L.-J. Tang W.-J. Lam F.-L. Lo W.-H. Yu W.-Y. Fan Q.-H. Chan ASC. Tetrahedron: Asymmetry 2007, 18: 2625

5j Deport C. Buchotte M. Abecassis K. Tadaoka H. Ayad T. Ohshima T. Genet J.-P. Mashima K. Ratovelomanana-Vidal V. Synlett 2007, 2743

5k Li Z.-W. Wang T.-L. He Y.-M. Wang Z.-J. Fan Q.-H. Pan J. Xu L.-J. Org. Lett. 2008, 10: 5265

5l Zhou H.-F. Li Z.-W. Wang Z.-J. Wang T.-L. Xu L.-J. He Y.-M. Fan Q.-H. Pan J. Gu L.-Q. Chan ASC. Angew. Chem. Int. Ed. 2008, 47: 8464

5m Lu S.-M. Bolm C. Adv. Synth. Catal. 2008, 350: 1101

5n Mršić N. Lefort L. Boogers JAF. Minnaard AJ. Feringa BL. de Vries JG. Adv. Synth. Catal. 2008, 350: 1081

5o Eggenstein M. Thomas A. Theuerkauf J. Franciò G. Leitner W. Adv. Synth. Catal. 2009, 351: 725

5p Wang C. Li C.-Q. Wu X.-F. Pettman A. Xiao J.-L. Angew. Chem. Int. Ed. 2009, 48: 6524

5q Tadaoka H. Cartigny D. Nagano T. Gosavi T. Ayad T. Genet J.-P. Ohshima T. Ratovelomanana-Vidal V. Mashima K. Chem. Eur. J. 2009, 15: 9990

5r Wang Z.-J. Zhou H.-F. Wang T.-L. He Y.-M. Fan Q.-H. Green Chem. 2009, 11: 767

5s Parekh V. Ramsden JA. Wills M. Tetrahedron: Asymmetry 2010, 21: 1549

5t Gou F.-R. Li W. Zhang XM. Liang Y.-M. Adv. Synth. Catal. 2010, 352: 2441

For the work on organocatalytic asymmetric hydrogenation of quinolines, see:

6a Rueping M. Antonchick AP. Theissmann T. Angew. Chem. Int. Ed. 2006, 45: 3683

6b Rueping M. Theissmann T. Raja S. Bats JWP. Adv. Synth. Catal. 2008, 350: 1001

6c Guo Q.-S. Du D.-M. Xu J. Angew. Chem. Int. Ed. 2008, 47: 759

For selected examples on asymmetric hydrogenation of other heteroaromatic compounds, see, for quinoxalines:

7a Cobley CJ. Henschke JP. Adv. Synth. Catal. 2003, 345: 195

7b Mršić N. Jerphagnon T. Minnaard AJ. Feringa BL. de Vries JG. Adv. Synth. Catal. 2009, 351: 2549

7c Tang W.-J. Xu L.-J. Fan Q.-H. Wang J. Fan B.-M. Zhou Z.-Y. Lam K.-H. Chan ASC. Angew. Chem. Int. Ed. 2009, 48: 9135

7d Cartigny D. Nagano T. Ayad T. Genet JP. Ohshima T. Mashima K. Ratovelomanana-Vidal V. Adv. Synth. Catal. 2010, 352: 1886

For furans, see:

7e Ohta T. Miyake T. Seido N. Kumobayashi H. Takaya H. J. Org. Chem. 1995, 60: 357

7f Kaiser S. Smidt SP. Pfaltz A. Angew. Chem. Int. Ed. 2006, 45: 5194

7g Feiertag P. Albert M. Nettekoven U. Spindler F. Org. Lett. 2006, 8: 4133

For pyridines, see:

7h Raynor SA. Thomas JM. Raja R. Johnson BFG. Belle RG. Mantle MD. Chem. Commun. 2000, 1925

7i Glorius F. Spielkamp N. Holle S. Goddard R. Lehmann CW. Angew. Chem. Int. Ed. 2004, 43: 2850

7j Legault CY. Charette AB. J. Am. Chem. Soc. 2005, 127: 8966

7k Wang X.-B. Zeng W. Zhou Y.-G. Tetrahedron Lett. 2008, 49: 4922

For indoles, see:

7l Kuwano R. Sato K. Kurokawa T. Karube D. Ito Y. J. Am. Chem. Soc. 2000, 122: 7614

7m Kuwano R. Kaneda K. Ito T. Sato K. Kurokawa T. Ito Y. Org. Lett. 2004, 6: 2213

7n Kuwano R. Kashiwabara M. Org. Lett. 2006, 8: 2653

7o Baeza A. Pfaltz A. Chem. Eur. J. 2010, 16: 2036

7p Wang D.-S. Chen Q.-A. Li W. Yu C.-B. Zhou Y.-G. Zhang XM. J. Am. Chem. Soc. 2010, 132: 8909

For pyrroles, see:

7q Kuwano R. Kashiwabara M. Ohsumi M. Kusano H. J. Am. Chem. Soc. 2008, 130: 808

8 Wang Z.-J. Deng G.-J. Li Y. He Y.-M. Tang W.-J. Fan Q.-H. Org. Lett. 2007, 9: 1243

9 Wang D.-S. Zhou J. Wang D.-W. Guo Y.-L. Zhou Y.-G. Tetrahedron Lett. 2010, 51: 525

10 Jahjah M. Alame M. Pellet-Rostaing S. Lemaire M. Tetrahedron: Asymmetry 2007, 18: 2305

11a Tang W.-J. Tan J. Xu L.-J. Lam K.-H. Fan Q.-H. Chan ASC. Adv. Synth. Catal. 2010, 352: 1055

11b Tang W.-J. Sun Y.-W. Xu L.-J. Wang T.-L. Fan Q.-H. Lam K.-H. Chan ASC. Org. Biomol. Chem. 2010, 8: 3464

12a Mamat C. Flemming A. Köckerling M. Steinbach J. Wuest FR. Synthesis 2009, 3311

12b Ishikawa S. Manabe K. Tetrahedron 2010, 66: 297

13 Michel B, Blandine L, and Sonia R. inventors; PCT Int. Appl. WO 2002012253.

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