Recent Applications of C1-Symmetric Bis(oxazoline)-Containing Ligands in Asymmetric Catalysis

Steven O’Reilly; Patrick J. Guiry

doi:10.1055/s-0033-1340829

Synthesis, Table of Contents

Synthesis 2014; 46(06): 722-739
DOI: 10.1055/s-0033-1340829

short review

Recent Applications of C ₁-Symmetric Bis(oxazoline)-Containing Ligands in Asymmetric Catalysis

Steven O’Reilly

Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland Fax: +353(1)7162501 Email: p.guiry@ucd.ie

,

Patrick J. Guiry*

Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Dublin 4, Ireland Fax: +353(1)7162501 Email: p.guiry@ucd.ie

› Author Affiliations

Abstract

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Abstract

Bis(oxazolines) are a well-known class of ligands in the area of asymmetric catalysis. Most of these ligands are C ₂-symmetric due to the synthetic route employed for their synthesis. This review article summarizes the recent progress of the closely related, but relatively unexplored, C ₁-symmetric bis(oxazoline) ligands and compares and contrasts the two where applicable.

1 Introduction

2 Bis(oxazolines)

2.1 Bis(oxazolines) with Differentially Substituted Oxazolines

2.2 Bis(oxazolines) with Asymmetrically Substituted Linking Unit

2.3 Bis(oxazolines) with Differentially Substituted Oxazolines and Asymmetrically Substituted Linking Unit

3 Conclusion

Key words

oxazoline - C ₁-symmetric - ligands - asymmetric catalysis - transition metals

Full Text

References

References
1 Brunner H, Obermann U, Wimmer P. J. Organomet. Chem. 1986; 316: C1
2 Ghosh AK, Mathivanan P, Cappiello J. Tetrahedron: Asymmetry 1998; 9: 1
3 McManus HA, Guiry PJ. Chem. Rev. 2004; 104: 4151
4 Desimoni G, Faita G, Jørgensen KA. Chem. Rev. 2006; 106: 3561
5 Hargaden GC, Guiry PJ. Chem. Rev. 2009; 109: 2505
6 Desimoni G, Faita G, Jørgensen KA. Chem. Rev. 2011; 111: PR284
7 Witte H, Seeliger W. Justus Liebigs Ann. Chem. 1974; 1974: 996
8 Reuman M, Meyers AI. Tetrahedron 1985; 41: 837
9 Nishiyama H, Soeda N, Naito T, Motoyama Y. Tetrahedron: Asymmetry 1998; 9: 2865
10 Cornejo A, Fraile JM, García JI, Gil MJ, Martínez-Merino V, Mayoral JA, Salvatella L. Angew. Chem. Int. Ed. 2005; 44: 458
11 Sibi MP, Venkatraman L, Liu M, Jasperse CP. J. Am. Chem. Soc. 2001; 123: 8444
12 Bull SD, Davies SG, Fox DJ, Garner AC, Sellers TG. R. Pure Appl. Chem. 1998; 70: 1501
13 Bull SD, Davies SG, Epstein SW, Ouzman JV. A. Chem. Commun. 1998; 659
14 Bull SD, Davies SG, Epstein SW, Leech MA, Ouzman JV. A. J. Chem. Soc., Perkin Trans. 1 1998; 2321
15 McManus HA, Guiry PJ. J. Org. Chem. 2002; 67: 8566
16 Lu S.-F, Du D.-M, Zhang S.-W, Xu J. Tetrahedron: Asymmetry 2004; 15: 3433
17 Hargaden GC, Guiry PJ In Innovative Catalysis in Organic Synthesis . Andersson PG. Wiley-VCH; Weinheim: 2012: 279
18 McManus HA, Cozzi PG, Guiry PJ. Adv. Synth. Catal. 2006; 348: 551
19 Hargaden GC, McManus HA, Cozzi PG, Guiry PJ. Org. Biomol. Chem. 2007; 5: 763
20 Coeffard V, Aylward M, Guiry PJ. Angew. Chem. Int. Ed. 2009; 48: 9152
21 García JI, Mayoral JA, Pires E, Villalba I. Tetrahedron: Asymmetry 2006; 17: 2270
22 Fraile JM, García JI, Gissibl A, Mayoral JA, Pires E, Reiser O, Roldán M, Villalba I. Chem. Eur. J. 2007; 13: 8830
23 Helmchen G, Pfaltz A. Acc. Chem. Res. 2000; 33: 336
24 Carroll MP, Guiry PJ, Brown JM. Org. Biomol. Chem. 2013; 11: 4591
25 Carroll MP, Guiry PJ. Chem. Soc. Rev. 2014; 43: 819
26 Garcia JI, Lopezsanchez B, Mayoral JA, Pires E, Villalba I. J. Catal. 2008; 258: 378
27 Orlandi S, Benaglia M, Dell’Anna G, Celentano G. J. Organomet. Chem. 2007; 692: 2120
28 Evans DA, Rovis T, Johnson JS. Pure Appl. Chem. 1999; 71: 1407
29 Atodiresei I, Schiffers I, Bolm C. Tetrahedron: Asymmetry 2006; 17: 620
30 For a synthesis of aza-bis(oxazoline) ligands, see: Werner H, Vicha R, Gissibl A, Reiser O. J. Org. Chem. 2003; 68: 10166
31 Lang K, Park J, Hong S. J. Org. Chem. 2010; 75: 6424
32 Ohshima T, Kawabata T, Takeuchi Y, Kakinuma T, Iwasaki T, Yonezawa T, Murakami H, Nishiyama H, Mashima K. Angew. Chem. Int. Ed. 2011; 50: 6296
33 Braunstein P, Naud F, Pfaltz A, Rettig SJ. Organometallics 2000; 19: 2676
34 Annunziata R, Benaglia M, Cinquini M, Cozzi F. Eur. J. Org. Chem. 2001; 1045
35 Annunziata R, Benaglia M, Cinquini M, Cozzi F, Puglisi A. Eur. J. Org. Chem. 2003; 1428
36 Annunziata R, Benaglia M, Cinquini M, Cozzi F, Pozzi G. Eur. J. Org. Chem. 2003; 1191
37 Mandoli A, Orlandi S, Pini D, Salvadori P. Chem. Commun. 2003; 2466
38 Zhou J, Ye M.-C, Tang Y. J. Comb. Chem. 2004; 6: 301
39 Deng C, Wang L.-J, Zhu J, Tang Y. Angew. Chem. Int. Ed. 2012; 51: 11620
40 Knight JG, Belcher PE. Tetrahedron: Asymmetry 2005; 16: 1415
41 Tan Q, Wen J, Li DL, Li H, You T. J. Mol. Catal. A: Chem. 2005; 242: 113
42 Seitz M, Capacchione C, Bellemin-Laponnaz S, Wadepohl H, Ward BD, Gade LH. Dalton Trans. 2006; 193
43 Bergbreiter DE, Tian J. Tetrahedron Lett. 2007; 48: 4499
44 Doherty S, Goodrich P, Hardacre C, Knight JG, Nguyen MT, Pârvulescu VI, Paun C. Adv. Synth. Catal. 2007; 349: 951
45 Burke AJ, da Palma Carreiro E, Chercheja S, Moura NM. M, Prates Ramalho JP, Rodrigues AI, dos Santos CI. M. J. Organomet. Chem. 2007; 692: 4863
46 Carreiro EP, Burke AJ, Ramalho JP. P, Rodrigues AI. Tetrahedron: Asymmetry 2009; 20: 1272
47 Sun Y.-J, Li N, Zheng Z.-B, Liu L, Yu Y.-B, Qin Z.-H, Fu B. Adv. Synth. Catal. 2009; 351: 3113
48 Zhuang W, Hansen T, Jørgensen KA. Chem. Commun. 2001; 347
49 Zhou J, Tang Y. J. Am. Chem. Soc. 2002; 124: 9030
50 Zhou J, Ye M.-C, Huang Z.-Z, Tang Y. J. Org. Chem. 2004; 69: 1309
51 Zhou J, Tang Y. Chem. Commun. 2004; 432
52 Rasappan R, Hager M, Gissibl A, Reiser O. Org. Lett. 2006; 8: 6099
53 Schätz A, Rasappan R, Hager M, Gissibl A, Reiser O. Chem. Eur. J. 2008; 14: 7259
54 Poulsen TB, Jørgensen KA. Chem. Rev. 2008; 108: 2903
55 Liu L, Zhao Q, Du F, Chen H, Qin Z, Fu B. Tetrahedron: Asymmetry 2011; 22: 1874
56 Liu L, Ma H, Fu B. Molecules 2012; 17: 1992
57 Liu L, Ma H, Xiao Y, Du F, Qin Z, Li N, Fu B. Chem. Commun. 2012; 48: 9281
58 Hargaden GC, O’Sullivan TP, Guiry PJ. Org. Biomol. Chem. 2008; 6: 562
59 Chollet G, Didier D, Schulz E. Catal. Commun. 2010; 11: 351
60 Didier D, Schulz E. Synlett 2012; 23: 1309
61 Didier D, Magnier-Bouvier C, Schulz E. Adv. Synth. Catal. 2011; 353: 1087
62 Castillo MR, Castillón S, Claver C, Fraile JM, Gual A, Martín M, Mayoral JA, Sola E. Tetrahedron 2011; 67: 5402
63 Sprinz J, Helmchen G. Tetrahedron Lett. 1993; 34: 1769
64 Manna K, Everett WC, Schoendorff G, Ellern A, Windus TL, Sadow AD. J. Am. Chem. Soc. 2013; 135: 7235

Recent Applications of C 1-Symmetric Bis(oxazoline)-Containing Ligands in Asymmetric Catalysis

Recent Applications of C ₁-Symmetric Bis(oxazoline)-Containing Ligands in Asymmetric Catalysis