18 J. E. Baldwin and S. J. Bonacorsi, J. Am. Chem. Soc., 1996, 118, 8258–
8265; J. E. Baldwin and S. J. Bonacorsi, J. Org. Chem., 1994, 59, 7401–
7409.
Acknowledgements
Acknowledgements are made to the donors of The Petroleum
Research Fund, administered by the ACS, for partial support of
this research, and we thank the National Science Foundation for
support of this work through CHE-0211120 and CHE-0514376.
19 E. J. Corey, P. D. Jardine, S. Virgil, P.-W. Yuen and R. D. Connell, J. Am.
Chem. Soc., 1989, 111, 9243–9244.
20 M. A. Lapitskaya and K. K. Pivnitsky, Russ. Chem. Bull., 1997, 46,
96–100.
21 K. Harada and T. Hayakawa, Bull. Chem. Soc. Jpn., 1964, 37, 191–194.
22 N. Takamura, T. Mizoguchi, K. Koga and S. Yamada, Tetrahedron,
1975, 31, 227–230.
References
23 T. Saegusa, Y. Ito and S. Kobayashi, Bull. Chem. Soc. Jpn., 1969, 42,
3535–3538.
1 E. Buchner and J. Geronimus, Ber. Dtsch. Chem. Ges., 1903, 36, 3782–
3786.
2 A. Burger and W. L. Yost, J. Am. Chem. Soc., 1948, 70, 2198–2201.
3 H. Nozaki, S. Moriuti, H. Takaya and R. Noyori, Tetrahedron Lett.,
1966, 5239–5244.
4 Y. Inouye, T. Sugita and H. M. Walborsky, Tetrahedron, 1964, 20,
1695–1699.
5 T. Aratani, Y. Nakanisi and H. Nozaki, Tetrahedron, 1970, 26, 1675–
1684.
6 H. Nozaki, H. Takaya, S. Moriuti and R. Noyori, Tetrahedron, 1968,
24, 3655–3669.
7 T. Aratani, Y. Yoneyoshi and T. Nagase, Tetrahedron Lett., 1975, 1707–
1710; T. Aratani, Y. Yoneyoshi and T. Nagase, Tetrahedron Lett., 1977,
2599–2602; T. Aratani, Y. Yoneyoshi and T. Nagase, Tetrahedron Lett.,
1982, 685–688; T. Aratani, Pure Appl. Chem., 1985, 57, 1839–1844.
8 For an intramolecular example of such asymmetric cyclopropanations,
see: H. Hirai and M. Matsui, Agric. Biol. Chem., 1976, 40, 169–174.
9 P. E. Krieger and J. A. Landgrebe, J. Org. Chem., 1978, 43, 4447–4452.
10 S. Kanemasa, S. Hamura, E. Harada and H. Yamamoto, Tetrahedron
Lett., 1994, 35, 7985–7988; H. Fritschi, U. Leutenegger and A. Pfaltz,
Helv. Chim. Acta, 1988, 71, 1553–1565.
24 For a sampling of synthetic routes to the isotopically labeled styrenes,
and of mechanistic studies utilizing them, see, inter alia: J. E. Baldwin
and J. A. Kapecki, J. Am. Chem. Soc., 1970, 92, 4874–4879; R. M.
Roberts and L. W. Elrod, J. Org. Chem., 1981, 46, 3732–3735; W. S.
Trahanovsky and M. E. Scribner, J. Am. Chem. Soc., 1984, 106, 7976–
7978; M. Julia and J.-P. Stacino, Bull. Soc. Chim. Fr., 1985, 831–832;
N. H. Werstiuk and G. Timmins, Can. J. Chem., 1986, 64, 1072–
1076; F.-D. Kopinke, G. Zimmermann, J. Aust and K. Scherzer, Chem.
Ber., 1989, 122, 721–725; J. F. Hartwig, R. G. Bergman and R. A.
Andersen, J. Am. Chem. Soc., 1991, 113, 3404–3418; G. Zimmermann,
B. Ondruschka, M. Nuechter, F.-D. Kopinke and M. Remmler, J. Prakt.
Chem., 1994, 336, 415–420; T. Rasmussen, J. F. Jensen, N. Østergaard,
D. Tanner, T. Ziegler and P.-O. Norrby, Chem. Eur. J., 2002, 8, 177–
184; C. P. Casey and N. A. Strotman, J. Am. Chem. Soc., 2004, 126,
1699–1704.
25 D. Seebach, R. Ha¨ssig and J. Gabriel, Helv. Chim. Acta, 1983, 66,
308–337.
26 J.-O. Baeg and H. Alper, J. Am. Chem. Soc., 1994, 116, 1220–1224.
27 H. G. Kuivila and O. F. Beumel, Jr., J. Am. Chem. Soc., 1961, 83,
1246–1250.
28 T. Nonaka, Y. Okuda, S. Matsubara, K. Oshima, K. Utimoto and H.
Nozaki, J. Org. Chem., 1986, 51, 4716–4718.
29 G. J. M. van der Kerk and J. C. Noltes, J. Appl. Chem., 1959, 9, 106–
113.
11 H. Nishiyama, Y. Itoh, Y. Sugawara, H. Matsumoto, K. Aoki and K.
Itoh, Bull. Chem. Soc. Jpn., 1995, 68, 1247–1262; H.-L. Kwong and
W.-S. Lee, Tetrahedron: Asymmetry, 2000, 11, 2299–2308; C.-M. Che,
J.-S. Huang, F.-W. Lee, Y. Li, T.-S. Lai, H.-L. Kwong, P.-F. Teng, W.-S.
Lee, W.-C. Lo, S.-M. Peng and Z.-Y. Zhou, J. Am. Chem. Soc., 2001,
123, 4119–4129.
30 J. P. Quintard and M. Pereyre, J. Labelled Compd. Radiopharm., 1978,
14, 653–661.
31 A. Liard and I. Marek, J. Org. Chem., 2000, 65, 7218–7220.
32 A. Sera, N. Ueda, K. Itoh and H. Yamada, Heterocycles, 1996, 43,
2205–2214.
12 For comprehensive summaries of the development and use of copper(II)
catalysts for cyclopropanation reactions and the contribution they have
made to progress in asymmetric organic synthesis as a whole, see:
J. Salau¨n, Chem. Rev., 1989, 89, 1247–1270; H. M. L. Davies and
E. G. Antoulinakis, Org. React., 2001, 57, 1–326; P. Vogel, Handb.
Exp. Pharmacol., 2003, 153, 3–44; A. Pfaltz, in Transition Metals for
Organic Synthesis, vol. 1, 2nd edn, ed. M. Beller and C. Bolm, Wiley-
VCH, Weinheim, 2004, pp. 157–170.
13 T. Sugita and Y. Inouye, Bull. Chem. Soc. Jpn., 1966, 39, 1075–1076;
J. E. Baldwin, J. Lo¨liger, W. Rastetter, N. Neuss, L. L. Huckstep and N.
De La Higuera, J. Am. Chem. Soc., 1973, 95, 3796–3797 (please note an
Addition and Correction in J. Am. Chem. Soc., 1973, 95, 6511–6512).
14 G. D. Andrews and J. E. Baldwin, J. Am. Chem. Soc., 1976, 98, 6705–
6706.
15 (a) J. E. Baldwin and C. G. Carter, J. Am. Chem. Soc., 1978, 100, 3942–
3944; (b) J. E. Baldwin and C. G. Carter, J. Am. Chem. Soc., 1979, 101,
1325–1326; (c) J. E. Baldwin and C. G. Carter, J. Am. Chem. Soc., 1982,
104, 1362–1368; (d) J. E. Baldwin and C. G. Carter, J. Org. Chem., 1983,
48, 3912–3917.
16 J. E. Baldwin and G. E. C. Chang, Tetrahedron, 1982, 38, 825–835.
17 J. E. Baldwin and T. C. Barden, T. C., J. Am. Chem. Soc., 1984, 106,
5312–5319; J. E. Baldwin and T. C. Barden, J. Am. Chem. Soc., 1984,
106, 6364–6367.
33 A. Liguori, P. Mascaro, G. Sindona and N. Uccella, J. Labelled Compd.
Radiopharm., 1990, 28, 1277–1283.
34 H.-I. Lee, A. F. Dexter, Y.-C. Fann, F. J. Lakner, L. P. Hager and B. M.
Hoffman, J. Am. Chem. Soc., 1997, 119, 4059–4069.
35 H.-S. Choi and R. L. Kuczkowski, J. Org. Chem., 1985, 50, 901–902.
36 A. J. Y. Lan, R. O. Heuckeroth and P. S. Mariano, J. Am. Chem. Soc.,
1987, 109, 2738–2745.
37 K. Nozaki, N. Sato, Y. Tonomura, M. Yasutomi, H. Takaya, T. Hiyama
and N. Koga, J. Am. Chem. Soc., 1997, 119, 12779–12795.
38 K. Nozaki, K. Oshima and K. Utimoto, J. Am. Chem. Soc., 1987, 109,
2547–2549; K. Nozaki, K. Oshima and K. Utimoto, Tetrahedron, 1989,
45, 923–933.
39 Dictionary of Organic Compounds, 6th edn, ed. J. Buckingham and
F. Macdonald, Chapman & Hall/Cambridge University Press, New
York, 1996, vol. 5, p. 5244, P-0-01768.
40 A. F. Cockerill, S. Rottschaefer and W. H. Saunders, Jr., J. Am. Chem.
Soc., 1967, 89, 901–905.
41 T. J. de Boer and H. J. Backer, Org. Synth., Coll. Vol. IV, 1963, 250–253.
42 J. Kang, G. J. Lim, S. K. Yoon and M. Y. Kim, J. Org. Chem., 1995, 60,
564–577.
2784 | Org. Biomol. Chem., 2006, 4, 2777–2784
This journal is
The Royal Society of Chemistry 2006
©