2048 K. Ohmatsu, T. Ooi / Tetrahedron Letters 56 (2015)
2043–2048
be ascribed to the ability of ion-paired ligand 20 to control
eitherthe distribution of syn and anti p-allyl palladium complexes
orthe relative rate of their bond formations.
Our group subsequently established a method for the in
situgeneration of ion-paired chiral ligands from hydrogen sulfate
saltsof ammonium phosphines and chiral Brønsted acids under
phase-transfer conditions. This technique was effectively utilized
for theiterative deconvolution screening of ion-paired chiral
ligands inasymmetric palladium catalysis. After only 16
experiments, thebest of 144 ligands could be identified to achieve
the first highlyenantioselective allylation of benzothiophenones
(Scheme 15).38
Conclusions
Although miscellaneous chiral supramolecular ligands havebeen
developed, it would be fair to state that this field is still inits
infancy and there remains much room for further development.First,
the synthesis of each component for self-assembly is
ratherdifficult in many cases. Second, the search for non-covalent
inter-actions suitable for creating supramolecular chiral ligands
is animportant task. Finally, most of supramolecular strategies
areapplied toward well-established asymmetric transformations,
suchas asymmetric hydrogenation of alkenes. Therefore, using
self-assembled chiral ligands to challenge hitherto difficult
asymmetricbond-forming reactions is essential to expand the
frontiers ofsupramolecular catalysis.
Acknowledgements
This work was supported by CREST from JST, Grants-in-Aid
forScientific Research (C) from JSPS, Program for Leading
GraduateSchools ‘Integrative Graduate Education and Research
Program inGreen Natural Sciences’ in the Nagoya University, the
TatematsuFoundation, and the Uehara Memorial Foundation.
References and notes
1. Comprehensive Asymmetric Catalysis, and Supplements 1 and 2;
Jacobsen, E. N.,Pfaltz, A., Yamamoto, H., Eds.; Springer, 1999,
2004.
2. Yoon, T. P.; Jacobsen, E. N. Science 2003, 299, 1691.3.
Groeger, H. In Catalytic Asymmetric Synthesis; Ojima, I., Ed.; John
Wiley & Sons:
New York, 2008.4. Selected recent reviews on asymmetric
enzymatic catalysis, see: (a) Reetz, M. T.
J. Org. Chem. 2009, 74, 5767; (b) Reetz, M. T. Angew. Chem.,
Int. Ed. 2011, 50, 138;(c) Müller, M. Adv. Synth. Catal. 2012, 354,
3161.
5. (a) Crabtree, R. H. Chem. Commun. 1999, 1611; (b) Gennari,
C.; Piarulli, U. Chem.Rev. 2003, 103, 3071; (c) Jäkel, C.;
Paciello, R. Chem. Rev. 2006, 106, 2912.
6. For reviews on mass spectrometry-based high-throughput
screening, see: (a)Chen, P. Angew. Chem., Int. Ed. 2003, 42, 2832;
(b) Müller, C. A.; Markert, C.;Teichert, A. M.; Pfaltz, A. Chem.
Commun. 2009, 1607; (c) Schröder, D. Acc. Chem.Res. 2012, 45,
1521.
7. For selected reports on high-throughput screening, see: (a)
Taylor, S. J.;Morken, J. P. Science 1998, 280, 267; (b) Jarvo, E.
R.; Evans, C. A.; Copeland, G. T.;Miller, S. J. J. Org. Chem. 2001,
66, 5522; (c) Evans, M. A.; Morken, J. P. J. Am.Chem. Soc. 2002,
124, 9020; (d) Reetz, M. T.; Tielmann, P.; Eipper, A.; Ross,
A.;Schlotterbeck, G. Chem. Commun. 2004, 1366; (e) Miller, C. A.;
Pfaltz, A. Angew.Chem., Int. Ed. 2008, 47, 3363; (f) Wassenaar, J.;
Jansen, E.; van Zeist, W.-J.;Bickelhaupt, F. M.; Siegler, M. A.;
Spek, A. L.; Reek, J. N. H. Nat. Chem. 2010, 2,417; (g) Ebner, C.;
Müller, C. A.; Markert, C.; Pfaltz, A. J. Am. Chem. Soc. 2011,133,
4710; (h) Lichtor, P. A.; Miller, S. J. ACS Comb. Sci. 2011, 13,
321.
8. Supramolecular Catalysis; van Leeuwen, P. W. N. M., Ed.;
Wiley-VCH: Weinheim,2008.
9. (a) Wilkinson, M. J.; van Leeuwen, P. W. N. M.; Reek, J. N.
H. Org. Biomol. Chem.2005, 3, 2371; (b) Breit, B. Angew. Chem.,
Int. Ed. 2005, 44, 6816; (c) Reetz, M. T.Angew. Chem., Int. Ed.
2008, 47, 2556; (d) Meeuwissen, J.; Reek, J. N. H. Nat.Chem. 2010,
2, 615; (e) Carboni, S.; Gennari, C.; Pignataro, L.; Piarulli, U.
DaltonTrans. 2011, 40, 4355; (f) Bellini, R.; van der Vlugt, J. I.;
Reek, J. N. H. Isr. J. Chem.2012, 52, 613; (g) Kirkorian, K.;
Ellis, A.; Twyman, L. J. Chem. Soc. Rev. 2012, 41,6138; (h) Kataev,
E. A.; Müller, C. Tetrahedron 2014, 70, 137; (i) Raynal,
M.;Ballester, P.; Vidal-Ferran, A.; van Leeuwen, P. W. N. M. Chem.
Soc. Rev. 2014, 43,
1660; (j) Raynal, M.; Ballester, P.; Vidal-Ferran, A.; van
Leeuwen, P. W. N. M.Chem. Soc. Rev. 2014, 43, 1734.
10. (a) Dang, T.-P.; Kagan, H. B. J. Chem. Soc. D 1971, 481; (b)
Kagan, H. B.; Dang, T.-P. J. Am. Chem. Soc. 1972, 94, 6429; (c)
Poulin, J.-C.; Dang, T.-P.; Kagan, H. B. J.Organomet. Chem. 1975,
84, 87.
11. Privileged Chiral Ligands and Catalysts; Zhou, Q.-L., Ed.;
Wiley-VCH: Weinheim,Germany, 2011.
12. Slagt, V. F.; van Leeuwen, P. W. N. M.; Reek, J. N. H. Chem.
Commun. 2003, 2474.13. (a) Walter, C. J.; Anderson, H. L.; Sanders,
J. K. M. J. Chem. Soc., Chem. Commun.
1993, 458; (b) Mackay, L. G.; Wylie, R. S.; Sanders, J. K. M. J.
Am. Chem. Soc.1994, 116, 3141; (c) Morris, G. A.; Nguyen, S. T.;
Hupp, J. T. J. Mol. Catal. A 2001,174, 15; (d) Merlau, M. L.; del
Pilar Mejia, M.; Nguyen, S. T.; Hupp, J. T. Angew.Chem., Int. Ed.
2001, 40, 4239.
14. (a) Slagt, V. F.; Röder, M.; Kamer, P. C. J.; van Leeuwen,
P. W. N. M.; Reek, J. N. H.J. Am. Chem. Soc. 2004, 126, 4056; (b)
Reek, J. N. H.; Röder, M.; Goudriaan, P. E.;Kamer, P. C. J.; van
Leeuwen, P. W. N. M.; Slagt, V. F. J. Organomet. Chem. 2005,690,
4505.
15. Jiang, X.-B.; Lefort, L.; Goudriaan, P. E.; de Vries, A. H.
M.; van Leeuwen, P. W. N.M.; de Vries, J. G.; Reek, J. N. H. Angew.
Chem., Int. Ed. 2006, 45, 1223.
16. Takacs, J. M.; Reddy, D. S.; Moteki, S. A.; Wu, D.;
Palencia, H. J. Am. Chem. Soc.2004, 126, 4494.
17. (a) Takacs, J. M.; Chaiseeda, K.; Moteki, S. A.; Reddy, D.
S.; Wu, D.; Chandra, K.Pure Appl. Chem. 2006, 78, 501; (b) Moteki,
S. A.; Liu, Z.; Ma, J.; Holmes, A. E.;Takacs, J. M. Chem. Commun.
2012, 263; (c) Moteki, S. A.; Takacs, J. M. Angew.Chem., Int. Ed.
2008, 47, 894.
18. Weis, M.; Waloch, C.; Seiche, W.; Breit, B. J. Am. Chem.
Soc. 2006, 128, 4188.19. (a) Birkholz, M.-N.; Dubrovina, N. V.;
Jiao, H.; Michalik, D.; Holz, J.; Paciello, R.;
Breit, B.; Börner, A. Chem. Eur. J. 2007, 13, 5896; (b)
Birkholz, M.-N.; Dubrovina,N. V.; Shuklov, I. A.; Holz, J.;
Paciello, R.; Waloch, C.; Breit, B.; Börner, A.Tetrahedron:
Asymmetry 2007, 18, 2055.
20. Wieland, J.; Breit, B. Nat. Chem. 2010, 2, 832.21. (a)
Laungani, A. C.; Breit, B. Chem. Commun. 2008, 844; (b) Laungani,
A. C.;
Slattery, J. M.; Krossing, I.; Breit, B. Chem. Eur. J. 2008, 14,
4488.22. (a) Sandee, A. J.; van der Burg, A. M.; Reek, J. N. H.
Chem. Commun. 2007, 864;
(b) Meeuwissen, J.; Kuil, M.; van der Burg, A. M.; Sandee, A.
J.; Reek, J. N. H.Chem. Eur. J. 2009, 15, 10272; (c) Meeuwissen,
J.; Detz, R.; Sandee, A. J.; deBruin, B.; Siegler, M. A.; Spek, A.
L.; Reek, J. N. H. Eur. J. Inorg. Chem. 2010, 2992;(d) Meeuwissen,
J.; Sandee, A. J.; de Bruin, B.; Siegler, M. A.; Spek, A. L.; Reek,
J.N. H. Organometallics 2010, 29, 2413.
23. Pignataro, L.; Carboni, S.; Civera, M.; Colombo, R.;
Piarulli, U.; Gennari, C.Angew. Chem., Int. Ed. 2010, 49, 6633.
24. (a) Patureau, F. W.; Kuil, M.; Sandee, A. J.; Reek, J. N. H.
Angew. Chem., Int. Ed.2008, 47, 3180; (b) Patureau, F. W.; de Boer,
S.; Kuil, M.; Meeuwissen, J.; Breuil,P.-A. R.; Siegler, M. A.;
Spek, A. L.; Sandee, A. J.; de Bruin, B.; Reek, J. N. H. J.
Am.Chem. Soc. 2009, 131, 6683.
25. (a) Liu, Y.; Sandoval, C. A.; Yamaguchi, Y.; Zhang, X.;
Wang, Z.; Kato, K.; Ding, K.J. Am. Chem. Soc. 2006, 128, 14212; (b)
Breuil, P.-A. R.; Patureau, F. W.; Reek, J.N. H. Angew. Chem., Int.
Ed. 2009, 48, 2162.
26. Pignataro, L.; Lynikaite, B.; Cvengroš, J.; Marchini, M.;
Piarulli, U.; Gennari, C.Eur. J. Org. Chem. 2009, 2539.
27. (a) Hattori, G.; Hori, T.; Miyake, Y.; Nishibayashi, Y. J.
Am. Chem. Soc. 2007, 129,12930; (b) Li, Y.; Feng, Y.; He, Y.-M.;
Chen, F.; Pan, J.; Fan, Q.-H. Tetrahedron Lett.2008, 49, 2878; (c)
Li, Y.; Ma, B.; He, Y.; Zhang, F.; Fan, Q.-H. Chem. Asian J.
2010,5, 2454.
28. Slagt, V. F.; Kaiser, P.; Berkessel, A.; Kuil, M.; Kluwer,
A. M.; van Leeuwen, P. W.N. M.; Reek, J. N. H. Eur. J. Inorg. Chem.
2007, 4653.
29. (a) Bellini, R.; Chikkali, S. H.; Berthon-Gelloz, G.; Reek,
J. N. H. Angew. Chem., Int.Ed. 2011, 50, 7342; (b) Gadzikwa, T.;
Bellini, R.; Dekker, H. L.; Reek, J. N. H. J. Am.Chem. Soc. 2012,
134, 2860.
30. Hatano, M.; Mizuno, T.; Izumiseki, A.; Usami, R.; Asai, T.;
Akakura, M.; Ishihara,K. Angew. Chem., Int. Ed. 2011, 50,
12189.
31. (a) Ishihara, K.; Kobayashi, J.; Inanaga, K.; Yamamoto, H.
Synlett 2001, 394; (b)Futatsugi, K.; Yamamoto, H. Angew. Chem.,
Int. Ed. 2005, 44, 1484.
32. Dydio, P.; Rubay, C.; Gadzikwa, T.; Lutz, M.; Reek, J. N. H.
J. Am. Chem. Soc. 2011,133, 17176.
33. van Leeuwen, P. W. N. M.; Rivillo, D.; Raynal, M.; Freixa,
Z. J. Am. Chem. Soc.2011, 133, 18562.
34. (a) Ohmatsu, K.; Ito, M.; Kunieda, T.; Ooi, T. Nat. Chem.
2012, 4, 473; See also:(b) Ohmatsu, K.; Imagawa, N.; Ooi, T. Nat.
Chem. 2014, 6, 47; (c) Ohmatsu, K.;Kawai, S.; Imagawa, N.; Ooi, T.
ACS Catal. 2014, 4, 4304.
35. Chiral phosphoric acids have been widely used as efficient
catalysts forasymmetric reactions. For reviews, see: (a) Akiyama,
T. Chem. Rev. 2007, 107,5744; (b) Terada, M. Chem. Commun. 2008,
4097; (c) Terada, M. Synthesis 2010,1929.
36. Recent reviews on asymmetric catalysis with chiral anions,
see: (a) Phipps,R. J.; Hamilton, G. L.; Toste, F. D. Nat. Chem.
2012, 4, 603; (b) Mahlau, M.;List, B. Angew. Chem., Int. Ed. 2013,
52, 518; For a review on asymmetric ion-pairing catalysis, see: (c)
Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013,52, 534.
37. (a) Ohmatsu, K.; Ito, M.; Ooi, T. Chem. Commun. 2014, 4554;
See also: (b)Ohmatsu, K.; Ito, M.; Kunieda, T.; Ooi, T. J. Am.
Chem. Soc. 2013, 135, 590.
38. Ohmatsu, K.; Hara, Y.; Ooi, T. Chem. Sci. 2014, 5, 3645.
http://refhub.elsevier.com/S0040-4039(15)00377-9/h0005http://refhub.elsevier.com/S0040-4039(15)00377-9/h0005http://refhub.elsevier.com/S0040-4039(15)00377-9/h0010http://refhub.elsevier.com/S0040-4039(15)00377-9/h0015http://refhub.elsevier.com/S0040-4039(15)00377-9/h0015http://refhub.elsevier.com/S0040-4039(15)00377-9/h0020http://refhub.elsevier.com/S0040-4039(15)00377-9/h0020http://refhub.elsevier.com/S0040-4039(15)00377-9/h0025http://refhub.elsevier.com/S0040-4039(15)00377-9/h0030http://refhub.elsevier.com/S0040-4039(15)00377-9/h0035http://refhub.elsevier.com/S0040-4039(15)00377-9/h0040http://refhub.elsevier.com/S0040-4039(15)00377-9/h0040http://refhub.elsevier.com/S0040-4039(15)00377-9/h0045http://refhub.elsevier.com/S0040-4039(15)00377-9/h0050http://refhub.elsevier.com/S0040-4039(15)00377-9/h0050http://refhub.elsevier.com/S0040-4039(15)00377-9/h0055http://refhub.elsevier.com/S0040-4039(15)00377-9/h0055http://refhub.elsevier.com/S0040-4039(15)00377-9/h0060http://refhub.elsevier.com/S0040-4039(15)00377-9/h0060http://refhub.elsevier.com/S0040-4039(15)00377-9/h0065http://refhub.elsevier.com/S0040-4039(15)00377-9/h0065http://refhub.elsevier.com/S0040-4039(15)00377-9/h0070http://refhub.elsevier.com/S0040-4039(15)00377-9/h0070http://refhub.elsevier.com/S0040-4039(15)00377-9/h0075http://refhub.elsevier.com/S0040-4039(15)00377-9/h0075http://refhub.elsevier.com/S0040-4039(15)00377-9/h0080http://refhub.elsevier.com/S0040-4039(15)00377-9/h0080http://refhub.elsevier.com/S0040-4039(15)00377-9/h0085http://refhub.elsevier.com/S0040-4039(15)00377-9/h0085http://refhub.elsevier.com/S0040-4039(15)00377-9/h0090http://refhub.elsevier.com/S0040-4039(15)00377-9/h0090http://refhub.elsevier.com/S0040-4039(15)00377-9/h0090http://refhub.elsevier.com/S0040-4039(15)00377-9/h0095http://refhub.elsevier.com/S0040-4039(15)00377-9/h0095http://refhub.elsevier.com/S0040-4039(15)00377-9/h0100http://refhub.elsevier.com/S0040-4039(15)00377-9/h0105http://refhub.elsevier.com/S0040-4039(15)00377-9/h0105http://refhub.elsevier.com/S0040-4039(15)00377-9/h0110http://refhub.elsevier.com/S0040-4039(15)00377-9/h0110http://refhub.elsevier.com/S0040-4039(15)00377-9/h0115http://refhub.elsevier.com/S0040-4039(15)00377-9/h0120http://refhub.elsevier.com/S0040-4039(15)00377-9/h0120http://refhub.elsevier.com/S0040-4039(15)00377-9/h0125http://refhub.elsevier.com/S0040-4039(15)00377-9/h0125http://refhub.elsevier.com/S0040-4039(15)00377-9/h0130http://refhub.elsevier.com/S0040-4039(15)00377-9/h0130http://refhub.elsevier.com/S0040-4039(15)00377-9/h0135http://refhub.elsevier.com/S0040-4039(15)00377-9/h0135http://refhub.elsevier.com/S0040-4039(15)00377-9/h0140http://refhub.elsevier.com/S0040-4039(15)00377-9/h0140http://refhub.elsevier.com/S0040-4039(15)00377-9/h0145http://refhub.elsevier.com/S0040-4039(15)00377-9/h0150http://refhub.elsevier.com/S0040-4039(15)00377-9/h0150http://refhub.elsevier.com/S0040-4039(15)00377-9/h0150http://refhub.elsevier.com/S0040-4039(15)00377-9/h0155http://refhub.elsevier.com/S0040-4039(15)00377-9/h0155http://refhub.elsevier.com/S0040-4039(15)00377-9/h0160http://refhub.elsevier.com/S0040-4039(15)00377-9/h0165http://refhub.elsevier.com/S0040-4039(15)00377-9/h0165http://refhub.elsevier.com/S0040-4039(15)00377-9/h0170http://refhub.elsevier.com/S0040-4039(15)00377-9/h0170http://refhub.elsevier.com/S0040-4039(15)00377-9/h0175http://refhub.elsevier.com/S0040-4039(15)00377-9/h0175http://refhub.elsevier.com/S0040-4039(15)00377-9/h0180http://refhub.elsevier.com/S0040-4039(15)00377-9/h0185http://refhub.elsevier.com/S0040-4039(15)00377-9/h0185http://refhub.elsevier.com/S0040-4039(15)00377-9/h0190http://refhub.elsevier.com/S0040-4039(15)00377-9/h0190http://refhub.elsevier.com/S0040-4039(15)00377-9/h0195http://refhub.elsevier.com/S0040-4039(15)00377-9/h0195http://refhub.elsevier.com/S0040-4039(15)00377-9/h0200http://refhub.elsevier.com/S0040-4039(15)00377-9/h0200http://refhub.elsevier.com/S0040-4039(15)00377-9/h0205http://refhub.elsevier.com/S0040-4039(15)00377-9/h0205http://refhub.elsevier.com/S0040-4039(15)00377-9/h0210http://refhub.elsevier.com/S0040-4039(15)00377-9/h0210http://refhub.elsevier.com/S0040-4039(15)00377-9/h0210http://refhub.elsevier.com/S0040-4039(15)00377-9/h0215http://refhub.elsevier.com/S0040-4039(15)00377-9/h0215http://refhub.elsevier.com/S0040-4039(15)00377-9/h0220http://refhub.elsevier.com/S0040-4039(15)00377-9/h0220http://refhub.elsevier.com/S0040-4039(15)00377-9/h0225http://refhub.elsevier.com/S0040-4039(15)00377-9/h0225http://refhub.elsevier.com/S0040-4039(15)00377-9/h0230http://refhub.elsevier.com/S0040-4039(15)00377-9/h0230http://refhub.elsevier.com/S0040-4039(15)00377-9/h0235http://refhub.elsevier.com/S0040-4039(15)00377-9/h0235http://refhub.elsevier.com/S0040-4039(15)00377-9/h0240http://refhub.elsevier.com/S0040-4039(15)00377-9/h0245http://refhub.elsevier.com/S0040-4039(15)00377-9/h0245http://refhub.elsevier.com/S0040-4039(15)00377-9/h0250http://refhub.elsevier.com/S0040-4039(15)00377-9/h0250http://refhub.elsevier.com/S0040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Design of supramolecular chiral ligands for asymmetric metal
catalysisIntroductionSupramolecular bidentate chiral ligands by
assemAssembly of chiral ligands with achiral buildingAchiral
ligands with chiral subcomponents
(Fig. ConclusionsAcknowledgementsReferences and notes