X. Zhao et al. / Tetrahedron 65 (2009) 512–517
517
4.2.2.4. (R)-2-((R,E)-1,3-Diphenylallyl)cyclopentanone(10b). 1H NMR
(CDCl3, 400 Hz): 1.70–1.86 (m,1H),1.94–2.11 (m, 3H), 2.18–2.28 (m,
L.; Dai, L. X. Angew. Chem., Int. Ed. 2006, 45, 5246–5248; (f) Braun, M.; Meier, T.
Angew. Chem., Int. Ed. 2006, 45, 6952–6955; (g) Zhan, L.; Shengming, Ma Angew.
Chem., Int. Ed. 2008, 47, 258–297.
d
1H), 2.29–2.38 (m,1H), 2.58–2.64 (m,1H), 4.05–4.10 (m,1H), 6.44 (d,
3. For a general review of enantioselective reactions of metal enolates, see: (a)
Comprehensive Asymmetric Catalysis III; Jacobsen, E. N., Pfaltz, A., Yamamoto, H.,
Eds.; Springer: Berlin, 1999; (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.;
Wiley-VCH: New York, NY, 2000; pp 465–697; (c) Modern Aldol Reactions;
Mahrwald, R., Ed.; Wiley-VCH: Weinheim, Germany, 2004; Vols. 1 and 2.
4. (a) Trost, B. M.; Self, C. R. J. Org. Chem. 1984, 49, 468–473; (b) Carfagna, C.;
Mariani, L.; Musco, A.; Sallese, G. J. Org. Chem. 1991, 56, 3924–3927; (c) Trost, B.
M.; Schroeder, G. M. J. Am. Chem. Soc. 1999, 121, 6759–6760; (d) Braun, M.;
Laicher, F.; Meier, T. Angew. Chem., Int. Ed. 2000, 39, 3494–3497; (e) Trost, B. M.;
Schroeder, G. M.; Kristensen, J. Angew. Chem., Int. Ed. 2002, 41, 3492–3495; (f)
Kazmaier, U. Curr. Org. Chem. 2003, 7, 317–328; (g) Burger, E. C.; Tunge, J. A. Org.
Lett. 2004, 6, 4113–4115; (h) Behenna, D. C.; Stoltz, B. M. J. Am. Chem. Soc. 2004,
126, 15044–15045; (i) Yan, X. X.; Liang, C. G.; Zhang, Y.; Hong, W.; Cao, B. X.;
Dai, L. X.; Hou, X. L. Angew. Chem., Int. Ed. 2005, 44, 6544–6546; (j) Trost, B. M.;
Xu, J. J. Am. Chem. Soc. 2005, 127, 17180–17181; (k) Graening, T.; Hartwig, J. F. J.
Am. Chem. Soc. 2005, 127, 17192–17193; (l) Trost, B. M.; Schroeder, G. M. Chem.
dEur. J. 2005, 11, 174–184; (m) Trost, B. M.; Frederiksen, M. U. Angew. Chem., Int. Ed.
2005, 44, 308–310; (n) Braun, M.; Meier, T. Synlett 2006, 661–676; (o) Trost, B. M.;
Xu, J.; Reichle, M. J. Am. Chem. Soc. 2007, 129, 282–283; (p) Be´langer, E.; Cantin,
K.; Messe, O.; Tremblay, M.; Paquin, J.-F. J. Am. Chem. Soc. 2007, 129, 1034–1035;
(q) Zheng, W. H.; Zheng, B. H.; Zhang, Y.; Hou, X. L. J. Am. Chem. Soc. 2007, 129,
7718–7719.
J¼3.2 Hz, 1H), 6.45 (s, 1H), 7.20–7.41 (m, 10H). 13C NMR (CDCl3,
100 Hz):
d 21.0, 26.1, 39.1, 48.0, 55.1, 126.4, 126.6, 128.7, 129.2, 129.3,
132.5, 132.6, 132.7, 137.4, 143.1, 219.3. HRMS (EI) calcd for C20H20
O
275.1514; found 275.1515.
4.2.2.5. (S)-2-((R,E)-1,3-Diphenylallyl)cycloheptanone (12a). 1H NMR
(CDCl3, 400 Hz): 1.23–1.28 (m, 4H), 1.62–1.66 (m, 2H), 1.85–1.88
d
(m, 2H), 2.44–2.49 (m, 2H), 3.06–3.12 (m, 1H), 3.80–3.84 (dd, J¼6.4,
10 Hz, 1H), 6.34–6.36 (m, 2H), 7.24–7.37 (m, 10H). 13C NMR (CDCl3,
100 Hz):
d 24.6, 28.5, 29.0, 29.8, 43.5, 51.4, 57.4, 126.5, 126.9, 127.4,
128.6, 128.6, 128.9, 130.9, 132.0, 137.5, 142.0, 215.1.
4.2.2.6. (R)-2-((R,E)-1,3-Diphenylallyl)cycloheptanone (12b). 1H NMR
(CDCl3, 400 Hz): d 1.20–1.39 (m, 4H),1.63–1.72 (m, 2H),1.83–1.89 (m,
2H), 2.23–2.34 (m, 2H), 3.03–3.12 (m, 1H), 3.81–3.86 (t, J¼9.6 Hz,
1H), 6.27–6.33 (dd, J¼10, 16 Hz, 1H), 6.45(d, J¼16 Hz, 1H), 7.13–7.35
(m, 10H). 13C NMR (CDCl3, 100 Hz):
d 24.1, 28.8, 29.0, 29.6, 44.1, 51.4,
5. Stork, G. Abstracts of the XVIth National Organic Symposium, Seattle, June,
1959, p 52.
56.9, 126.5, 126.6, 127.5, 127.8, 128.7, 128.8, 131.0, 131.8, 137.4, 143.1,
214.9. HRMS (EI) calcd for C22H24O 304.1827; found 304.1829.
6. Selected reviews: (a) Hickmott, P. W. Tetrahedron 1982, 38, 1975–2050; (b)
Enamines: Synthesis, Structure, and Reactions; Cook, A. G., Ed.; Marcel Dekker:
New York, NY, 1988; pp 1–101; (c) Modern Aldol Reactions; Mahrwald, R., Ed.;
Wiley-VCH: Weinheim, Germany, 2004; Vol. 1, pp 161–200; Selected papers:
(d) Yamada, S.; Hiroi, K.; Achiwa, K. Tetrahedron Lett. 1969, 10, 4233–4236; (e)
Matsushita, H.; Noguchi, M.; Yoshikawa, S. Bull. Chem. Soc. Jpn. 1976, 49, 1928–
1930; (f) Whitesell, J. K.; Felman, S. W. J. Org. Chem. 1977, 42, 1663–1664; (g)
Tomioka, K.; Ando, K.; Yasuda, K.; Koga, K. Tetrahedron Lett. 1986, 27, 715–716;
(h) Duthaler, R. O. Angew. Chem., Int. Ed. 2003, 42, 975–978; (i) Merino, P.;
Tejero, T. Angew. Chem., Int. Ed. 2004, 43, 2995–2997.
4.2.2.7. (E)-2-(1,3-Diphenylallyl)-2,3-dihydro-1H-inden-1-one (14a
and 14b). 1H NMR (CDCl3, 400 Hz):
d 2.90–3.30 (m, 6H), 4.14–4.21
(t, 1H), 4.34–4.41 (dd, J¼2.8, 7.6 Hz, 1H), 6.21–6.74 (m, 4H), 7.11–
7.78 (m, 28H). HRMS (EI) calcd for C24H20O 324.1514; found
324.1511.
7. Momiyama, N.; Yamamoto, H. J. Am. Chem. Soc. 2005, 127, 1080–1081.
8. (a) Hiroi, K.; Abe, J.; Suya, K.; Sato, S.; Koyama, T. J. Org. Chem. 1994, 59, 203–
213; (b) Ibrahem, I.; Co´rdova, A. Angew. Chem., Int. Ed. 2006, 45, 1952–1956.
9. Part of results have been communicated: Liu, D. L.; Xie, F.; Zhang, W. Tetrahe-
dron Lett. 2007, 48, 7591–7594; And after the manuscript of the communication
was completed, an Ir-catalyzed asymmetric allylic alkylation with enamines
was appeared: Weix, D. J.; Hartwig, J. F. J. Am. Chem. Soc. 2007, 129, 7720–7721.
10. (a) Ferrocenes; Hayashi, T., Togni, A., Eds.; Wiley-VCH: Weinheim, Germany,
1995; (b) Metallocenes; Togni, A., Haltermann, R. L., Eds.; Wiley-VCH: Wein-
heim, Germany, 1998; (c) Dai, L. X.; Tu, T.; You, S. L.; Deng, W. P.; Hou, X. L. Acc.
Chem. Res. 2003, 36, 659–667; (d) Colacot, T. J. Chem. Rev. 2003, 103, 3101–3118.
11. (a) Zhang, W.; Adachi, Y.; Hirao, T.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7,
451–460; (b) Zhang, W.; Hirao, T.; Ikeda, I. Tetrahedron Lett. 1996, 37, 4545–
4548.
4.2.2.8. 2-(Cyclohex-2-enyl)cyclohexanone (17a and 17b). 1H NMR
(CDCl3, 400 Hz):
d
1.05–2.41 (m, 15H), 2.52–2.75 (m, 1H), 5.35–5.52
21.9, 22.1,
(m, 1H), 5.59–5.72 (m, 1H). 13C NMR (CDCl3, 100 Hz):
d
24.8, 24.0, 25.2, 25.3, 25.4, 27.2, 28.0, 28.2, 29.5, 29.9, 33.5, 34.2,
42.4, 42.5, 55.1, 55.8, 128.2, 128.4, 129.0, 131.0, 213.0.
Acknowledgements
This work was partly supported by the National Natural Science
Foundation of China and Nippon Chemical Industrial Co., Ltd.
12. (a) Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron Lett. 1996, 37, 7995–
7998; (b) Zhang, W.; Shimanuki, T.; Kida, T.; Nakatsuji, Y.; Ikeda, I. J. Org. Chem.
1999, 64, 6247–6251.
Supplementary data
13. Liu, D. L.; Xie, F.; Zhang, W. Tetrahedron Lett. 2007, 48, 585–588.
14. Liu, D. L.; Xie, F.; Zhao, X.; Zhang, W. Tetrahedron 2008, 64, 3561–3566.
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Supplementary data associated with this article can be found in
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