216
S. Doherty et al. / Tetrahedron: Asymmetry 23 (2012) 209–216
19. Mullen, C. A.; Gagné, M. R. Org. Lett. 2006, 8, 665–668.
NMR (75.5 MHz, CDCl3, d): 167.1 (C@O), 140.8 (q, C4H2S), 132.2
(C4H2S), 126.4 (C4H2S), 124.5 (C4H2S), 120.0 (q, JC-F = 283.0 Hz,
CF3), 76.9 (q, JC-F = 26.8 Hz, CCF3), 63.9 (OCH2), 14.9 (OCH2CH3),
13.8 (CH3); LRMS (EI) m/z 268 [MꢁH]+. Retention times: tR of major
(R)-enantiomer = 43.1 min; tR of minor (S)-enantiomer = 43.7 min;
67% ee. Absolute stereochemistry assigned by analogy.
20. Corkey, B. K.; Toste, D. F. J. Am. Chem. Soc. 2005, 127, 17168–17169.
21. (a) Phua, P. H.; de Vries, J. D.; Hii, K. K. Adv. Synth. Catal. 2005, 347, 1775–1780;
(b) Li, K.; Cheng, X.; Hii, K. K. Eur. J. Org. Chem. 2004, 959–964; (c) Hamashima,
Y.; Somei, H.; Shimura, Y.; Tamura, T.; Sodeoka, M. Org. Lett. 2004, 6, 1861–
1864.
22. For highly informative reviews see: (a) Hamashima, Y.; Sodeoka, M. Chem. Recl.
2004, 4, 231; (b) Sodeoka, M.; Hamashima, Y. Bull. Chem. Soc. Jpn. 2005, 78,
941–956. and references cited therein.
23. (a) Aikawa, K.; Hioki, Y.; Mikami, K. J. Am. Chem. Soc. 2009, 131, 13922–13923;
(b) Aikawa, K.; Hioki, Y.; Mikami, K. Org. Lett. 2010, 12, 5716–5719.
24. Fukushima, M.; Takushima, D.; Kimura, M. J. Am. Chem. Soc. 2010, 132, 16346–
16348.
25. (a) Chianese, A. R.; Lee, S. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2007, 46, 4042–
4059; (b) Fürstner, A.; Davies, P. W. Angew. Chem., Int. Ed. 2007, 46, 3410–3449;
(c) Michelet, V.; Toullec, P. Y.; Genet, J.-P. Angew. Chem., Int. Ed. 2007, 47, 4268–
4315.
Acknowledgments
We gratefully acknowledge Johnson Matthey for generous loans
of platinum group metal salts, Newcastle University for funding
(H.M.-Z) and the EPSRC National Mass Spectrometry Service Centre
in Swansea.
26. For NUPHOS diphosphines see: (a) Doherty, S.; Knight, J. G.; Robins, E. G.;
Scanlan, T. H.; Champkin, P. A.; Clegg, W. J. Am. Chem. Soc. 2001, 123, 5110–
5111; (b) Doherty, S.; Robins, E. G.; Nieuwenhuyzen, M.; Knight, J. G.;
Champkin, P. A.; Clegg, W. Organometallics 2002, 21, 1383–1399; (c) Doherty,
S.; Newman, C. R.; Rath, R. K.; van den Berg, J.-A.; Hardacre, C.;
Nieuwenhuyzen, M.; Knight, J. G. Organometallics 2004, 23, 1055–1064; (d)
Doherty, S.; Newman, C. R.; Rath, R. K.; Luo, H.-K.; Nieuwenhuyzen, M.; Knight,
J. G. Org. Lett. 2003, 5, 3863–3866; (e) Doherty, S.; Newman, C. R.;
Nieuwenhuyzen, M.; Knight, J. G. Organometallics 2003, 22, 1452–1462; (f)
Doherty, S.; Knight, J. G.; Hardacre, C.; Luo, H.-K.; Newman, C. R.;
Nieuwenhuyzen, M. Organometallics 2004, 23, 6127–6133; (g) Doherty, S.;
Newman, C. R.; Rath, R. K.; Nieuwenhuyzen, M.; Knight, J. G.; Clegg, W.
Organometallics 2005, 24, 2633–2644; for NUBIPHEP diphosphines see: (h)
Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. Org. Lett.
2007, 9, 4925–4928; (i) Doherty, S.; Smyth, C. H.; Harrington, R. W.; Clegg, W.
Organometallics 2008, 27, 4837–4840; (j) Doherty, S.; Smyth, C. H.; Harrington,
R. W.; Clegg, W. Organometallics 2008, 27, 4837–4840; for KITPHOS
monophosphines see: (k) Doherty, S.; Knight, J. G.; Smyth, C. H.; Jorgensen,
G. A. Adv. Synth. Catal. 2008, 350, 1801–1806; (l) Doherty, S.; Knight, J. G.;
McGrady, J. P.; Ferguson, A. M.; Ward, N. A. B.; Harrington, R. W.; Clegg, W. Adv.
Synth. Catal. 2010, 352, 201–211; (m) Doherty, S.; Knight, J. G.; Hashmi, A. S. K.;
Smyth, C. H.; Ward, N. A. B.; Robson, K. J.; Tweedley, S.; Harrington, R. W.;
Clegg, W. Organometallics 2010, 29, 4139–4147.
References
1. For general reviews on enantioselective ene reactions see: (a) Mikami, K.;
Shimizu, M. Chem. Rev. 1992, 92, 1021–1050; (b) Dias, L. Curr. Org. Chem. 2000,
4, 305–342; (c) Berrisford, D. J.; Bolm, C. Angew. Chem., Int. Ed. 1995, 34, 1717–
1719; (d) Mikami, K.; Terada, M. In Comprehensive Asymmetric Catalysis;
Springer: Berlin,Heidelberg, 1999; Vol. III, p 1143; (e) Mikami, K.; Nakai, T.
Catalytic Asymmetric Synthesis; Wiley-VCH: New York, 2000. pp 543–568; (f)
Clarke, M. L.; France, M. B. Tetrahedron 2008, 64, 9003–9031.
2. Mikami, K.; Kawakami, Y.; Akiyama, K.; Aikawa, K. J. Am. Chem. Soc. 2007, 129,
12950–12951.
3. Brekan, J. A.; Reynolds, T. E.; Scheidt, K. A. J. Am. Chem. Soc. 2010, 132, 1472–
1473.
4. Maruoka, K.; Hoshino, Y.; Chirasaka, Y. H.; Yamamoto, H. Tetrahedron Lett.
1988, 29, 3967–3970.
5. (a) Mikami, K. Pure Appl. Chem. 1996, 68, 639–644; (b) Mikami, K.; Terada, M.;
Nakai, T. J. Am. Chem. Soc. 1990, 112, 3949–3954; (c) Mikami, K.; Matsukawa, S.
J. Am. Chem. Soc. 1993, 115, 7039–7040; (d) Mikami, K.; Yajima, T.; Terada, M.;
Kato, E.; Maruta, M. Tetrahedron: Asymmetry 1994, 5, 1087–1090; (e) Mikami,
K.; Tomoko, Y.; Takasaki, T.; Matsukawa, S.; Terada, M.; Uchimaru, T.; Maruta,
M. Tetrahedron 1996, 52, 85–98; (f) Yuan, Y.; Zhang, X.; Ding, K. Angew Chem.,
Int. Ed. 2003, 42, 5478–5480; (g) Sekiguti, T.; Iizuka, Y.; Takizawa, S.;
Jayaprakash, D.; Arai, T.; Sasai, H. Org. Lett. 2003, 5, 2647–2650.
6. (a) Evans, D. A.; Tregay, S. W.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T. J. Am.
Chem. Soc. 2000, 122, 7936–7943; (b) Caplan, N. A.; Hancock, F. E.; Bulman
Page, P. C.; Hutchings, G. J. Angew. Chem., Int. Ed. 2004, 43, 1685–1688; (c) Gao,
Y.; Lane-Bell, P.; Vederas, J. C. J. Org. Chem. 1998, 63, 2133–2143.
7. Langner, M.; Remy, P.; Bolm, C. Synlett 2005, 781–784.
27. For CATPHOS diphosphines see: (a) Doherty, S.; Knight, J. G.; Smyth, C. H.;
Harrington, R. W.; Clegg, W. Organometallics 2008, 27, 1679–1682; (b) Doherty,
S.; Smyth, C. H.; Harrimann, A.; Harrington, R. W.; Clegg, W. Organometallics
2009, 28, 888–895.
28. Doherty, S.; Knight, J. G.; Bell, A. L.; El-Menabawey, S.; Vogels, C. M.; Decken, A.;
Westcott, S. Tetrahedron: Asymmetry 2009, 20, 1437–1444.
29. (a) Hao, J.; Hatano, H.; Mikami, K. Org. Lett. 2000, 2, 4059–4062; (b) Doherty, S.;
Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W. Organometallics 2007,
26, 5961–5966.
8. (a) Hutson, G. E.; Dave, A. H.; Rawal, V. H. Org. Lett. 2007, 9, 3869–3872; (b)
Kezuka, S.; Ikeno, T.; Yamada, T. Org. Lett. 2001, 3, 1937–1939.
9. (a) Ruck, R. T.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 2882–2883; (b) Ruck,
R. T.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2003, 42, 4771–4774; (c) Grachan, M.
L.; Tudge, M. T.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2008, 47, 1469–1472.
10. (a) Zhao, J.-F.; Tjan, T.-B. W.; Tan, B.-H.; Loh, T.-P. Org. Lett. 2009, 11, 5714–
5716; (b) Zhao, J.-J.; Tan, B.-H.; Zhu, M.-K.; Tjan, T. B. W.; Loh, T.-P. Adv. Synth.
Catal. 2010, 352, 2085–2088; (c) Zhao, J.-F.; Tsui, H.-Y.; Wu, P.-J.; Lu, J.; Loh, T.-
P. J. Am. Chem. Soc. 2008, 130, 16492–16493.
11. (a) Evans, D. A.; Wu, J. J. Am. Chem. Soc. 2005, 127, 8006–8007; (b) Zhao, T.-J.; Li,
B.; Tan, L.-J. S.; Shen, X.-L.; Loh, T.-P. J. Am. Chem. Soc. 2010, 132, 10242–10244.
12. Zheng, K.; Shi, J.; Liu, X.; Feng, X. J. Am. Chem. Soc. 2008, 130, 15770–15771.
13. Rueping, M.; Theissmann, T.; Kuenkel, A.; Koenigs, R. M. Angew. Chem., Int. Ed.
2008, 47, 6798–6801.
30. (a) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478–
9479; (b) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagné, M. R. Organometallics
2000, 19, 4376–4384.
31. (a) Koh, J.-H.; Larsen, A. O.; Gagné, M. R. Org. Lett. 2001, 3, 1233–1236; (b)
Becker, J. J.; van Orden, L. J.; White, P. S.; Gagné, M. R. Org. Lett. 2002, 4, 727–
730; (c) Aikawa, K.; Mikami, K. Angew. Chem., Int. Ed. 2003, 42, 5458–5461; (d)
Aikawa, K.; Mikami, K. Angew. Chem. Int. Ed. 2003, 42, 5455–5458.
32. (a) Doherty, S.; Knight, J. G.; Smyth, C. H.; Harrington, R. W.; Clegg, W.
Organometallics 2007, 26, 6453–6461; (b) Doherty, S.; Knight, J. G.; Smyth, C.
H.; Harrington, R. W.; Clegg, W. J. Org. Chem. 2006, 71, 9751–9764; (c) Doherty,
S.; Goodrich, P.; Hardacre, C.; Luo, H.-K.; Nieuwenhuyzen, M.; Rath, R. K.
Organometallics 2005, 24, 5945–5955.
14. Oi, S.; Kashiwagi, K.; Inoue, Y. Tetrahedron Lett. 1998, 39, 6253–6256.
15. (a) Brunkan, N. M.; White, P. S.; Gagné, M. R. Organometallics 2002, 21, 1565–
1575; (b) Brunkan, N. M.; Gagné, M. R. Organometallics 2002, 21, 1576–1582;
(c) Brunkan, N. M.; Gagné, M. R. Organometallics 2002, 21, 4711–4717.
16. (a) Ghosh, A. K.; Matsuda, H. Org. Lett. 1999, 1, 2157–2159; (b) Pignat, K.;
Vallotto, J.; Pinna, F.; Strukul, G. Organometallics 2000, 19, 5160–5167.
17. (a) Becker, J. J.; Van Orden, L. J.; White, P. S.; Gagné, M. R. Org. Lett. 2002, 4, 727–
730; (b) Oi, S.; Terada, E.; Ohuchi, K.; Kato, T.; Tachibana, Y.; Inoue, Y.
Organometallics 1999, 64, 8660–8667; (c) Oi, S.; Kashiwaga, K.; Terada, E.;
Ohuchi, K.; Inoue, Y. Tetrahedron Lett. 1996, 37, 6351–6354; (d) Cendron, A.;
Strukul, G. J. Mol. Catal. A: Chem. 2003, 204, 187–193.
33. (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am.
Chem. Soc. 1998, 120, 5824–5825; (b) Evans, D. A.; Kozlowski, M. C.; Burgey, C.
S.; MacMillan, D. W. J. Am. Chem. Soc. 1997, 119, 7893–7894.
34. Mikami, K.; Kakuno, H.; Aikawa, K. Angew. Chem., Int. Ed. 2005, 44, 7257–7260.
35. (a) Zhuang, W.; Gathergood, N.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 2001,
66, 1009–1013; (b) Poulsen, T. B.; Jørgensen, K. A. Chem. Rev. 2008, 108, 2903–
2915.
36. Drew, D.; Doyle, J. R. Inorg. Synth. 1990, 28, 346–348.
37. (a) Lautens, M.; Kimanovic, S. J. Am. Chem. Soc. 1995, 117, 1954–1964; (b) Lara,
M.; Muttl, F. G.; Glueck, S. M.; Kroutil, W. Eur. J.Org. Chem. 2008, 3668–3672.
38. Kreyes, A.; Amirkhanl, M.; Lieberwirth, I.; Mauer, R.; Laqual, F.; Landfester, K.;
Ziener, U. Chem. Mat. 2010, 22, 6453–6458.
18. (a) Hori, K.; Ito, J.; Ohta, T.; Furukawa, I. Tetrahedron 1998, 54, 12737–12744;
(b) Hori, K.; Kodama, H.; Ohta, T.; Furukawa, I. J. Org. Chem. 1999, 64, 5017–
5023.