Pure and Applied Chemistry, 2008, Volume 80, No. 5, pp. 967-977, References

Pure Appl. Chem., 2008, Vol. 80, No. 5, pp. 967-977

http://dx.doi.org/10.1351/pac200880050967

Enantio- and regioselective CpRu-catalyzed Carroll rearrangement

Martina Austeri, Frederic Buron, Samuel Constant, Jerome Lacour, David Linder, Jessica Müller and Simone Tortoioli

Department of Organic Chemistry, University of Geneva, quai Ernest Ansermet 30, CH-1211 Geneva 4, Switzerland

References

1. (a). B. M. Trost, D. L. Van Vranken. Chem. Rev. 96, 395 (1996); (http://dx.doi.org/10.1021/cr9409804)
1. (b). P. J. Guiry, C. P. Saunders. Adv. Synth. Catal. 346, 497 (2004); (http://dx.doi.org/10.1002/adsc.200303138)
1. (c). S. W. Krska, D. L. Hughes, R. A. Reamer, D. J. Mathre, M. Palucki, N. Yasuda, Y. Sun, B. M. Trost. Pure Appl. Chem. 76, 625 (2004); (http://dx.doi.org/10.1351/pac200476030625)
1. (d). D. K. Leahy, P. A. Evans. Mod. Rhodium-Catal. Org. React. 191 (2005);
1. (e). H. Miyabe, Y. Takemoto. Synlett 1641 (2005);
1. (f). M. Braun, T. Meier. Angew. Chem., Int. Ed. 45, 6952 (2006); (http://dx.doi.org/10.1002/anie.200602169)
1. (g). G. Helmchen, A. Dahnz, P. Duebon, M. Schelwies, R. Weihofen. Chem. Commun. 6751 (2007).
2. C. Bruneau, J. L. Renaud, B. Demerseman. Chem.Eur. J. 12, 5178 (2006). (http://dx.doi.org/10.1002/chem.200600173)
3. B. M. Trost, P. L. Fraisse, Z. T. Ball. Angew. Chem., Int. Ed. 41, 1059 (2002). (http://dx.doi.org/10.1002/1521-3773(20020315)41:6<1059::AID-ANIE1059>3.0.CO;2-5)
4. (a). M. D. Mbaye, B. Demerseman, J. L. Renaud, L. Toupet, C. Bruneau. Angew. Chem., Int. Ed. 42, 5066 (2003); (http://dx.doi.org/10.1002/anie.200352257)
4. (b). J. L. Renaud, C. Bruneau, B. Demerseman. Synlett 408 (2003); (http://dx.doi.org/10.1055/s-2003-37120)
4. (c). M. D. Mbaye, B. Demerseman, J. L. Renaud, L. Toupet, C. Bruneau. Adv. Synth. Catal. 346, 835 (2004); (http://dx.doi.org/10.1002/adsc.200404023)
4. (d). M. D. Mbaye, B. Demerseman, J. L. Renaud, C. Bruneau. J. Organomet. Chem. 690, 2149 (2005); (http://dx.doi.org/10.1016/j.jorganchem.2005.02.002)
4. (e). B. Demerseman, J. L. Renaud, L. Toupet, C. Hubert, C. Bruneau. Eur. J. Inorg. Chem. 137 (2006).
5. (a). T. Kondo, H. Ono, N. Satake, T.-a. Mitsudo, Y. Watanabe. Organometallics 14, 1945 (1995); (http://dx.doi.org/10.1021/om00004a055)
5. (b). T. Kondo, Y. Morisaki, S.-y. Uenoyama, K. Wada, T.-a. Mitsudo. J. Am. Chem. Soc. 121, 8657 (1999); (http://dx.doi.org/10.1021/ja991704f)
5. (c). Y. Morisaki, T. Kondo, T. Mitsudo. Organometallics 18, 4742 (1999). (http://dx.doi.org/10.1021/om990533k)
6. (a). H. Kondo, Y. Yamaguchi, H. Nagashima. Chem. Commun. 1075 (2000); (http://dx.doi.org/10.1039/b002927k)
6. (b). H. Kondo, A. Kageyama, Y. Yamaguchi, M.-A. Haga, K. Kirchner, H. Nagashima. Bull. Chem. Soc. Jpn. 74, 1927 (2001); (http://dx.doi.org/10.1246/bcsj.74.1927)
6. (c). H. Nagashima, H. Kondo, T. Hayashida, Y. Yamaguchi, M. Gondo, S. Masuda, K. Miyazaki, K. Matsubara, K. Kirchner. Coord. Chem. Rev. 245, 177 (2003). (http://dx.doi.org/10.1016/S0010-8545(03)00124-3)
7. (a). R. Hermatschweiler, I. Fernandez, F. Breher, P. S. Pregosin, L. F. Veiros, M. J. Calhorda. Angew. Chem., Int. Ed. 44, 4397 (2005); (http://dx.doi.org/10.1002/anie.200500967)
7. (b). R. Hermatschweiler, I. Fernandez, P. S. Pregosin, E. J. Watson, A. Albinati, S. Rizzato, L. F. Veiros, M. J. Calhorda. Organometallics 24, 1809 (2005); (http://dx.doi.org/10.1021/om049057a)
7. (c). I. Fernandez, R. Hermatschweiler, F. Breher, P. S. Pregosin, L. F. Veiros, M. J. Calhorda. Angew. Chem., Int. Ed. 45, 6386 (2006); (http://dx.doi.org/10.1002/anie.200600447)
7. (d). I. Fernandez, R. Hermatschweiler, P. S. Pregosin, A. Albinati, S. Rizzato. Organometallics 25, 323 (2006); (http://dx.doi.org/10.1021/om050749o)
7. (e). I. Fernandez, P. S. Pregosin, A. Albinati, S. Rizzato. Organometallics 25, 4520 (2006); (http://dx.doi.org/10.1021/om060448u)
7. (f). R. Hermatschweiler, I. Fernandez, P. S. Pregosin, F. Breher. Organometallics 25, 1440 (2006). (http://dx.doi.org/10.1021/om051050l)
8. (a). E. C. Burger, J. A. Tunge. Org. Lett. 6, 2603 (2004); (http://dx.doi.org/10.1021/ol049097a)
8. (b). E. C. Burger, J. A. Tunge. Chem. Commun. 2835 (2005); (http://dx.doi.org/10.1039/b503568f)
8. (c). C. Wang, J. A. Tunge. Org. Lett. 7, 2137 (2005); (http://dx.doi.org/10.1021/ol050466s)
8. (d). J. A. Tunge, E. C. Burger. Eur. J. Org. Chem. 1715 (2005). (http://dx.doi.org/10.1002/ejoc.200400865)
9. (a). M. F. Carroll. J. Chem. Soc. 1266 (1940); (http://dx.doi.org/10.1039/jr9400001266)
9. (b). M. F. Carroll. J. Chem. Soc. 704 (1940); (http://dx.doi.org/10.1039/jr9400000704)
9. (c). M. F. Carroll. J. Chem. Soc. 507 (1941). (http://dx.doi.org/10.1039/jr9410000507)
10. (a). M. Defosseux, N. Blanchard, C. Meyer, J. Cossy. Org. Lett. 5, 4037 (2003); (http://dx.doi.org/10.1021/ol035177n)
10. (b). M. E. Jung, B. A. Duclos. Tetrahedron Lett. 45, 107 (2004); (http://dx.doi.org/10.1016/j.tetlet.2003.10.102)
10. (c). W. Bonrath, T. Netscher. Appl. Catal., A 280, 55 (2005) and refs. cited therein.
11. R. Kuwano, N. Ishida, M. Murakami. Chem. Commun. 3951 (2005). (http://dx.doi.org/10.1039/b505105c)
12. B. M. Trost. J. Org. Chem. 69, 5813 (2004). (http://dx.doi.org/10.1021/jo0491004)
13. (a). Y. Matsushima, K. Onitsuka, T. Kondo, T. Mitsudo, S. Takahashi. J. Am. Chem. Soc. 123, 10405 (2001); (http://dx.doi.org/10.1021/ja016334l)
13. (b). Y. Matsushima, K. Onitsuka, S. Takahashi. Organometallics 24, 2747 (2005). (http://dx.doi.org/10.1021/om0500523)
14. M. D. Mbaye, J. L. Renaud, B. Demerseman, C. Bruneau. Chem. Commun. 1870 (2004). (http://dx.doi.org/10.1039/b406039c)
15. Ligand 8 was still unable to accelerate the reaction catalyzed by 1b under the optimized conditions (0 % conv., 7d, THF, 60 degC, 0.5 M); compound 1b being prepared using Kundig's protocol: E. P. Kundig, F. R. Monnier. Adv. Synth. Catal. 346, 901 (2004). (http://dx.doi.org/10.1002/adsc.200404124)
16. (a). T. Asai, T. Aoyama, T. Shioiri. Synthesis 811 (1980); (http://dx.doi.org/10.1055/s-1980-29216)
16. (b). M. Cinquini, S. Colonna, F. Cozzi. J. Chem. Soc., Perkin Trans. 1 247 (1978); (http://dx.doi.org/10.1039/p19780000247)
16. (c). (R)-2,2-dimethyl-1-phenylpropan-1-amine: M. E. Warren, H. E. Smith. J. Am. Chem. Soc. 87, 1757 (1965); (http://dx.doi.org/10.1021/ja01086a026)
16. (d). V. V. Dunina, M. Y. Kazakova, Y. K. Grishin, O. R. Malyshev, E. I. Kazakova. Russ. Chem. Bull. 46, 1321 (1997). (http://dx.doi.org/10.1007/BF02495935)
17. G. Bernardinelli, D. Fernandez, R. Gosmini, P. Meier, A. Ripa, P. Schupfer, B. Treptow, E. P. Kundig. Chirality 12, 529 (2000). (http://dx.doi.org/10.1002/(SICI)1520-636X(2000)12:5/6<529::AID-CHIR41>3.0.CO;2-3)
18. The o-MeO substituent in 9h creates an A(1,3) strain situation with the neighboring stereogenic center; the increased rigidity of 9h vs. 9g is possibly the reason for the better selectivity. With the MeO group, 9h is also a potential tridentate ligand; the ether linkage functioning possibly as an "on-off"-ligand allowing for the formation of a s-allyl Ru-intermediate. We thank a referee for this latter suggestion.
19. (a). K. Soai, S. Yokoyama, T. Hayasaka, K. Ebihara. J. Org. Chem. 53, 4148 (1988); (http://dx.doi.org/10.1021/jo00252a063)
19. (b). A. Hajra, N. Yoshikai, E. Nakamura. Org. Lett. 8, 4153 (2006). (http://dx.doi.org/10.1021/ol0618306)
20. L. Alcaraz, J. J. Harnett, C. Mioskowski, J. P. Martel, T. Legall, D. S. Shin, J. R. Falck. Tetrahedron Lett. 35, 5449 (1994). (http://dx.doi.org/10.1016/S0040-4039(00)73522-2)
21. C. Hubert, J. L. Renaud, B. Demerseman, C. Fischmeister, C. Bruneau. J. Mol. Catal. A: Chem. 237, 161 (2005). (http://dx.doi.org/10.1016/j.molcata.2005.03.050)
22. S. Constant, S. Tortoioli, J. Muller, D. Linder, F. Buron, J. Lacour. Angew. Chem., Int. Ed. 46, 8979 (2007). (http://dx.doi.org/10.1002/anie.200704019)
23. S. Constant, R. Frantz, J. Muller, G. Bernardinelli, J. Lacour. Organometallics 26, 2141 (2007). (http://dx.doi.org/10.1021/om070074k)
24. TRISPHAT-N: [bis(tetrachlorobenzenediolato)mono(5-chloropyridine-2,3-diolato) phosphate(V)] anion. This anion 11 is chiral and was used as a racemate throughout this study.
25. Interestingly, no stable complex is formed by the addition of [Bu3NH][11] to [Cp*Ru(bpy)(NCCH3)][PF6].
26. Compound 12 has been fully characterized using classical spectroscopic and spectrometric means. See the supplementary material.
27. In the absence of 3b or 12, allylic ester 4a is thermally stable at 140 degC for at least 2 h with no trace of 12 or other isomers being observed: see Table 3, entry 1.
28. S. Constant, S. Tortoioli, J. Muller, J. Lacour. Angew. Chem., Int. Ed. 46, 2082 (2007). (http://dx.doi.org/10.1002/anie.200604573)
29. (a). B. Coq, F. Figueras. Coord. Chem. Rev. 178-180, 1753 (1998); (http://dx.doi.org/10.1016/S0010-8545(98)00058-7)
29. (b). E. K. Van Den Beuken, B. L. Feringa. Tetrahedron 54, 12985 (1998); (http://dx.doi.org/10.1016/S0040-4020(98)00319-6)
29. (c). M. Shibasaki, N. Yoshikawa. Chem. Rev. 102, 2187 (2002). (http://dx.doi.org/10.1021/cr010297z)
30. (a). T. J. Goodwin, R. S. Vagg, P. A. Williams. J. Proc. R. Soc. N. S. W. 117, 1 (1984);
30. (b). G. C. Van Stein, G. Van Koten, K. Vrieze, C. Brevard, A. L. Spek. J. Am. Chem. Soc. 106, 4486 (1984); (http://dx.doi.org/10.1021/ja00328a031)
30. (c). P. K. Bowyer, K. A. Porter, A. D. Rae, A. C. Willis, S. B. Wild. Chem. Commun. 1153 (1998); (http://dx.doi.org/10.1039/a800083b)
30. (d). C. R. Baar, L. P. Carbray, M. C. Jennings, R. J. Puddephatt, J. J. Vittal. Organometallics 20, 408 (2001); (http://dx.doi.org/10.1021/om0007769)
30. (e). Y. N. Belokon, M. North, T. D. Churkina, N. S. Ikonnikov, V. I. Maleev. Tetrahedron 57, 2491 (2001); (http://dx.doi.org/10.1016/S0040-4020(01)00072-2)
30. (f). S. Kano, H. Nakano, M. Kojima, N. Baba, K. Nakajima. Inorg. Chim. 349, 6 (2003); (http://dx.doi.org/10.1016/S0020-1693(03)00052-5)
30. (g). M. Klopstra, R. Hage, R. M. Kellogg, B. L. Feringa. Tetrahedron Lett. 44, 4581 (2003); (http://dx.doi.org/10.1016/S0040-4039(03)00979-1)
30. (h). S. Schoumacker, O. Hamelin, J. Pecaut, M. Fontecave. Inorg. Chem. 42, 8110 (2003); (http://dx.doi.org/10.1021/ic0346533)
30. (i). Q. T. Nguyen, J. H. Jeong. Polyhedron 25, 1787 (2006); (http://dx.doi.org/10.1016/j.poly.2005.11.028)
30. (j). A. Ouali, M. Taillefer, J.-F. Spindler, A. Jutand. Organometallics 26, 65 (2007); (http://dx.doi.org/10.1021/om060706n)
30. (k). J. Song, Q. Shen, F. Xu, X. Lu. Tetrahedron 63, 5148 (2007). (http://dx.doi.org/10.1016/j.tet.2007.04.006)
31. This result reflects the intrinsic instability of ligand 13 and its complexes 14. For this reason, recycling of complexes 15 or reactions under microwave irradiation was not attempted.

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Enantio- and regioselective CpRu-catalyzed Carroll rearrangement

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Enantio- and regioselective CpRu-catalyzed Carroll rearrangement

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