R. Ballini et al. / Tetrahedron Letters 44 (2003) 2271–2273
2273
−
1
1
pure 3g. IR w=3400, 1600, 1550 cm ; H NMR
CDCl ) l=1.5 (d, 3H, J=7.5 Hz), 1.7–1.9 (m, 2H),
5. Ono, N. In The Nitro Group in Organic Synthesis; Feuer,
H., Ed.; Wiley-VCH: New York, 2001.
(
3
2
7
.7–2.9 (m, 2H), 3.8–4.1 (m, 1H), 4.3–4.4 (m, 1H),
.1–7.3 (m, 5H). Anal. calcd for C H NO C, 63.14;
6. (a) Rosini, G. In Comprehensive Organic Synthesis; Trost,
B. M., Ed.; Pergamon: New York, 1992; pp. 321–340; (b)
Luzzio, F. A. Tetrahedron 2001, 57, 915–945.
1
1
15
3
H, 7.22; N, 6.69. Found: C, 63.00; H, 6.98; N, 6.90.
7
. Jouglet, B.; Bianco, L.; Rousseau, G. Synlett 1991, 907–
908.
. (a) Sera, A.; Takagi, K.; Katayama, H.; Yamada, H. J.
Org. Chem. 1988, 53, 1157–1161; (b) Misumi, Y.; Bul-
man, R. A.; Matsumoto, W. Heterocyclic 2002, 56, 599–
606.
Typical procedure (Michael reaction) for the formation
of 5b: 1-Nitropropane [187 mg, 2.1 mmol, (4.2 mmol
when the starting nitroalkane is nitroethane)] was
mixed with methyl vinyl ketone (122 mg, 2.1 mmol),
then, the catalyst KG-60-NEt2 (0.42 g) was added.
After standing (stirring can be avoided since it does not
change the efficiency of the reaction) at room tempera-
ture for the appropriate time (see Table 1) the mixture
was extracted with EtOAc (5×20 mL), the catalyst was
filtered off, the organic layer was evaporated and the
crude product was purified by flash chromatography
8
9
. Clark, J. H. Green Chem. 1999, 1, 1–8.
1
1
1
0. Sheldon, R. Chem. Ind. (London) 1997, 12–15.
1. Corma, A. Chem. Rev. 1995, 95, 559–614.
2. Thomas, J. M.; Raja, R.; Sankar, G.; Johnson, B. F. G.;
Lewis, D. W. Chem. Eur. J. 2001, 7, 2973–2978.
3. (a) Ballabeni, M.; Ballini, R.; Bigi, F.; Maggi, R.; Parrini,
M.; Predieri, G.; Sartori, G. J. Org. Chem. 1999, 64,
1
(
cyclohexane/EtOAc, 8:2), affording 247 mg (80%) of
−
1 1
the pure 5b. IR w=1710, 1545 cm ; H NMR (CDCl )
l=0.96 (t, 3H, J=7.0 Hz), 2.2 (s, 3H), 1.6–2.9 (m, 6H),
3
1029–1032; (b) Ballini, R.; Bigi, F.; Gogni, E.; Maggi, R.;
Sartori, G. J. Catal. 2000, 191, 348–353; (c) Ballini, R.;
Bosica, G.; Maggi, R.; Ricciutelli, M.; Righi, P.; Sartori,
G.; Sartorio, R. Green Chem. 2001, 3, 178–180; (d)
Ballini, R.; Bosica, G.; Fiorini, D.; Maggi, R.; Righi, P.;
Sartori, G.; Sartorio, R. Tetrahedron Lett. 2002, 43,
4
5
8
.4 (t, 1H, J=6.0 Hz). Anal. calcd for C H NO C,
2.82; H, 8.23; N, 8.80. Found: C, 53.04; H, 8.41; N,
.56.
7 13 3
8
445–8447.
Acknowledgements
1
4. Demicheli, G.; Maggi, R.; Mazzacani, A.; Righi, P.;
Sartori, G.; Bigi, F. Tetrahedron Lett. 2001, 42, 2401–
The work was carried out in the framework of the
National Project ‘Il Mezzo Acquoso nelle Applicazioni
Sintetiche dei Nitrocomposti Alifatici’ supported by
Ministero dell’Universit a` e della Ricerca Scientifica e
Tecnologica, Rome-Italy, by Fondazione della Cassa di
Risparmio della Provincia di Macerata and by the
University of Camerino and Parma.
2
404.
5. Rosini, G.; Ballini, R.; Petrini, M.; Sorrenti, P. Synthesis
985, 515–517.
1
1
1
6. (a) M e` lot, J.-M.; Texier-Boullet, F.; Foucaud, A. Tetra-
hedron Lett. 1986, 27, 493; (b) Hurd, C. D.; Nilson, M. E.
J. Org. Chem. 1955, 20, 927–936.
1
7. (a) Barrett, A. G. M.; Graboski, G. G. Chem. Rev. 1986,
86, 751–762; (b) Kabalka, G. W.; Varma, R. S. Org.
Prep. Proc. Int. 1987, 19, 283–328; (c) Ballini, R.; Castag-
nani, R.; Petrini, M. J. Org. Chem. 1992, 57, 2160–2162;
References
(
5
d) Ballini, R.; Palestini, C. Tetrahedron Lett. 1994, 35,
731–5734; (e) Perekalin, V. V.; Lipina, E. S.; Berestovit-
skaya, V. M.; Efremov, D. A. Nitroalkenes; John Wiley
Sons: Chichester, 1994.
8. Shenhav, H.; Rappoport, Z.; Patai, S. J. Chem. Soc. (B)
970, 469–476.
1
. Seebach, D.; Colvin, E. W.; Leher, F.; Weller, F.; Weller,
T. Chimia 1979, 33, 1–18.
2
3
. Rosini, G.; Ballini, R. Synthesis 1988, 833–847.
. Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P.
Org. Prep. Proc. Int. 1990, 22, 707–746.
&
1
1
4
. Ballini, R.; Bosica, G. Recent Development in Organic
Chemistry; Transworld Research Network: Trivandrum,
19. Cauvel, A.; Renard, G.; Brunel J. Org. Chem. 1997, 62,
749–751.
1
997; Vol. 1, pp. 11–24.