4
5
(a) M. Murakami, T. Itahashi and Y. Ito, J. Am. Chem. Soc., 2002, 124,
Notes and references
13976; (b) T. Matsuda, A. Fujimoto, M. Ishibashi and M. Murakami,
Chem. Lett., 2004, 33, 876.
(a) M. Murakami, S. Ashida and T. Matsuda, J. Am. Chem. Soc., 2005,
127, 6932; (b) M. Murakami, S. Ashida and T. Matsuda, J. Am. Chem.
Soc., 2006, 128, 2166.
For the spectral data of 2a, see: H. Morrison, K. Muthuramu,
G. Pandey, D. Severance and B. Bigot, J. Org. Chem., 1986, 51, 3358.
(a) S. Ogoshi, M.-a. Oka and H. Kurosawa, J. Am. Chem. Soc., 2004,
{
0
(
General procedure: A toluene solution (1.0 mL) of Ni(cod)
.020 mmol), P(c-Hex) (11.2 mg, 0.040 mmol) and 3-styrylcyclobutanone 1
0.20 mmol) was stirred in a Schlenk-type flask under nitrogen atmosphere
2
(5.5 mg,
3
at 100 uC for 2–12 h. The reaction mixture was cooled, concentrated, and
the residue was purified by preparative thin-layer chromatography of silica
gel (hexane : ethyl acetate) to afford the product 2.
6
7
1
26, 11802; (b) S. Ogoshi, M. Ueta, T. Arai and H. Kurosawa, J. Am.
1
2
3
For reviews, see: (a) R. H. Crabtree, Chem. Rev., 1985, 85, 245; (b)
M. Murakami and Y. Ito, in Activation of Unreactive Bonds and Organic
Synthesis; ed. S. Murai, Topics in Organometallic Chemistry, Springer,
Berlin, 1999, vol. 3, pp. 97–129; (c) M. E. van der Boom and D. Milstein,
Chem. Rev., 2003, 103, 1759; (d) C.-H. Jun, Chem. Soc. Rev., 2004, 33,
Chem. Soc., 2005, 127, 12810; (c) S.-S. Ng and T. F. Jamison, J. Am.
Chem. Soc., 2005, 127, 14194; (d) C.-Y. Ho, S.-S. Ng and T. F. Jamison,
J. Am. Chem. Soc., 2006, 128, 5362.
For b-carbon elimination from transition metal cyclobutanolate, see: (a)
T. Nishimura and S. Uemura, Synlett, 2004, 201; (b) T. Matsuda,
M. Shigeno, M. Makino and M. Murakami, Org. Lett., 2006, 8, 3379.
The structure of 5:
8
9
610–618.
For recent examples of catalytic and stoichiometric reactions, see: (a)
Y. Terao, M. Nomoto, T. Satoh, M. Miura and M. Nomura, J. Org.
Chem., 2004, 69, 6942; (b) P. Zhao and J. F. Hartwig, J. Am. Chem.
Soc., 2005, 127, 11618; (c) A. Funayama, T. Satoh and M. Miura, J. Am.
Chem. Soc., 2005, 127, 15354; (d) P. Zhao, C. D. Incarvito and
J. F. Hartwig, J. Am. Chem. Soc., 2006, 128, 3124.
For recent examples, see: (a) C. M u¨ ller, R. J. Lachicotte and W. D. Jones,
Organometallics, 2002, 21, 1975; (b) T. Kondo, Y. Taguchi, Y. Kaneko,
M. Niimi and T. Mitsudo, Angew. Chem., Int. Ed., 2004, 43, 5369; (c)
T. L. Dzwiniel and J. M. Stryker, J. Am. Chem. Soc., 2004, 126, 9184;
(d) S. Komagawa and S. Saito, Angew. Chem., Int. Ed., 2006, 45, 2446;
(
e) Y. Nakao, T. Yukawa, Y. Hirata, S. Oda, J. Satoh and T. Hiyama,
10 IPr 5 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene.
11 Although the relative configuration of 2c was not determined, it
was obtained as a single diastereoisomer (dr 5 .95 : 5) from 1c
(E : Z 5 .95 : 5).
J. Am. Chem. Soc., 2006, 128, 7116; (f) Y. Nakao, Y. Hirata and
T. Hiyama, J. Am. Chem. Soc., 2006, 128, 7420; (g) Y. Nakao, S. Oda,
A. Yada and T. Hiyama, Tetrahedron, 2006, 62, 7567.
This journal is ß The Royal Society of Chemistry 2006
Chem. Commun., 2006, 4599–4601 | 4601