1050
LETTERS
SYNLETT
References and Notes
(24) Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.;
1998
Rosati, O. Tetrahedron Lett.
, in press.
1980
, 261.
(1) Fisher, R. H.; Weitz, H. M. Synthesis
1984
(2) Ballini, R.; Sorrenti, P. Org. Prep. Proc. Int.
1983
, 16, 289.
(25) General procedure for the preparation of α,ω-dicarboxylic
acids (2) is as follows: To a solution of α-nitro ketone (0.7 mmol)
(3) Dampawan, P.; Zajac, W. W. Synthesis
, 545.
in MeOH (4.2 ml), 25 ml of 0.5 M Na HPO in a 1 N of NaOH
2
4
1993
, 34,
(4) Rathore, R.; Lin, Z.; Kochi, J. K. Tetrahedron Lett.
were added and the resulting mixture was heated at 70 °C for 1-4
1859.
®
h, then Oxone (1.75 mmol) in water (3 ml) was added to the cold
(5) Venkat Ram Reddy, M.; Kumareswaran, R.; Vankar, Y. D.
1995
solution (r. t.). After 4 h the mixture was diluted with brine (10
ml), acidified to pH=2 with a 10% solution of HCl and extracted
with EtOAc (3 x 20 ml). The combined organic layers were
Tetrahedron Lett.
(6) Stach, H.; Hesse, M. Tetrahedron
(7) Rosini, G.; Ballini, R.; Petrini, M.; Marotta, E.; Righi, P. Org.
1990
, 36, 7149.
1988
, 44, 1573.
washed with brine (10 ml), dried over Na SO and evaporated to
2
4
Prep. Proc. Int.
, 22, 707.
yield pure dicarboxylic acid 2.
1986
, 16, 1781.
(8) Ballini, R.; Petrini, M. Synthetic Commun.
(26) General procedure for the preparation of α,ω-dicarboxylic
acid monomethyl esters (3) is as follows: To a solution of α-nitro
ketone (0.7 mmol) in MeOH (2 ml), 6 ml of a solution of KOH
(1.75 mmol) in MeOH were added and the resulting mixture was
1992
, 355.
(9) Ballini, R.; Petrini, M.; Polzonetti, V. Synthesis
(10) Ballini, R.; Bartoli, G.; Giovannini, R.; Marcantoni, E.; Petrini, M.
1993
Tetrahedron Lett.
, 34, 3301.
heated at 65 °C for 4 h, then 17 ml of a 0.5 M of Na HPO in a 1
N solution of NaOH and Oxone (2.1 mmol) in water (5 ml) were
added to the cold solution r.t.). After 4 h the mixture was diluted
2
4
1988
(11) Ballini, R.; Marcantoni, E.; Petrini, M.; Rosini, G. Synthesis
,
®
915.
1990
, 46, 7531.
(12) Ballini, R.; Petrini, M.; Rosini, G. Tetrahedron
withwater(20ml)anda5%solutionofNaHCO (5ml),washedwith
3
1996
(13) Ballini, R.; Petrini, M.; Polimanti, O. J. Org. Chem.
, 61,
CH Cl (1 x 10 ml), acidified to pH=2 with a 1% solution of HCl
2
2
5652.
and extracted with EtOAc (3 x 20 ml). The combined layerswere
washed with brine 10 ml), dried over Na SO and evaporated
(14) Saika, A. K.; Hazarika, M.; Barua, N. C.; Bezbarua, M. S.;
2
4
1996
Sharma, R. P.; Ghosh, A. C. Synthesis
(15) Ballini, R.; Barboni, L.; Pintucci, L. Synlett
1997
, 981.
yielding the pure compound 3.
1997
, 1389.
3b,c,e
(27) Selected analytical data for the compounds
:
-1
1
(16) Ballini, R.; Bosica, G. Tetrahedron
(17) Murray, R. W.; Jeyaraman, R. J. Org. Chem.
1992
, 53, 16131.
3b: IR (CH Cl ): ν = 2890, 1730 and 1709 cm ; H NMR
2
2
1985
, 50, 2847.
(CDCl ): δ = 0.88 (s, 9H), 1.28-2.47 (m, 7H), 3.62 (s, 3H), 9.20-
3
9.80 (s br, 1H). Anal. Calcd. for C
H O : C, 61.09; H, 9.32.
11 20 4
(18) Greenlagh, R. P. Synlett
(19) Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.;
1995
, 235.
Found: C, 61.17; H, 9.40.
-1
1
3c: IR (CH Cl ): ν = 2890, 1740 and 1710 cm ; H NMR
2
2
Rosati, O. J. Org. Chem.
, 60, 8412.
(20) Denmark, S. E.; Forbes, D. C.; Hays, D. S.; De Pue, J. S.; Wilde,
1995
(CDCl ): δ = 0.85-0.97 (d, 3H, J = 5.9 Hz), 1.35-2.45 (m, 7H),
3
3.62 (s, 3H), 8.75-9.45 (s br, 1H). Anal. Calcd. for C H O : C,
8
14 4
R. G. J. J. Org. Chem.
(21) Hirano, M.; Oose, M. Morimoto, T. Chem. Lett.
(22) Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.;
1996
, 60, 1391.
55.16; H, 8.10. Found: C, 55.09; H, 8.16.
3e: IR (CH Cl ): ν = 2890, 1733 and 1710 cm ; H NMR
1991
, 331.
-1
1
2
2
(CDCl ): δ = 1.78-2.22 (m, 4H), 2.55-2.62 (d, 2H, J = 7.3 Hz),
3
Rosati, O. Synlett
(23) Ceccherelli, P.; Curini, M.; Epifano, F.; Marcotullio, M. C.;
1998
, 767.
2.96-3.08 (m, 1H), 3.53 (s, 3H), 7.10-7.27 (m, 5H), 9.25-9.75 (s
br, 1H). Anal. Calcd. for C
H O : C, 66.09; H, 6.82. Found: C,
13 16 4
Rosati, O. Synth. Commun.
, 28, in press.
66.17; H, 6.90.