2022
S. Karsch et al.
LETTER
Chem.–Eur. J. 1998, 4, 1480. (f) Chan, W. H.; Lee, A. W.
M.; Jiang, L. S.; Mak, T. C. W. Tetrahedron: Asymmetry
1997, 8, 2501.
sulfonate 5 in CH2Cl2 was added catalyst 2 in small portions
at 40 °C. The reaction conditions are listed in Table 2. After
the reaction had stopped, the solvent was evaporated and the
residue was purified by flash chromatography. Compound
6j: 1H NMR (500 MHz, CDCl3): = 1.71–1.76 (m, 2 H, 5-
H), 1.80–1.84 (m, 2 H, 6-H), 2.37–2.41 (m, 2 H, 4-H), 3.89
(d, J1,2 = 7.9 Hz, 2 H, 1-H), 4.36–4.38 (m, 2 H, 7-H), 5.60–
5.65 (m, 1 H, 2-H), 5.86–5.92 (m, 1 H, 3-H). 13C NMR
(125.8 MHz, CDCl3): = 24.85 (t, C-5), 25.98 (t, C-4), 26.47
(t, C-6), 49.43 (t, C-1), 73.51 (t, C-7), 115.96 (d, C-2),
139.57 (d, C-3).
(3) For current reviews on ring closing metathesis, see:
(a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34,
18. (b) Fürstner, A. Angew. Chem. Int. Ed 2000, 39, 3012;
Angew. Chem. 2000, 112, 3140. (c) Yet, L. Chem. Rev.
2000, 100, 2963.
(4) For ring closing metathesis to sultams, see: (a) Wanner, J.;
Harned, A. M.; Probst, D. A.; Poon, K. W. C.; Klein, T. A.;
Snelgrove, K. A.; Hanson, P. R. Tetrahedron Lett. 2002, 43,
917. (b) Lane, C.; Snieckus, V. Synlett 2000, 1294.
(c) Long, D. D.; Termin, A. P. Tetrahedron Lett. 2000, 41,
6743. (d) Brown, R. C. D.; Castro, J. L.; Moriggi, J.-D.
Tetrahedron Lett. 2000, 41, 3681. (e) Hanson, P. R.; Probst,
D. A.; Robinson, R. E.; Yau, M. Tetrahedron Lett. 1999, 40,
4761.
(5) (a) Rondestvedt, C. S. Jr. J. Am. Chem. Soc. 1954, 76, 1926.
(b) Truce, W. E.; Norell, J. R. J. Am. Chem. Soc. 1963, 85,
3231. (c) Dauban, P.; Dodd, R. H. Org. Lett. 2000, 2, 2327.
(6) For preparation of 4e, see: Brunel, Y.; Rousseau, G. J. Org.
Chem. 1996, 61, 5793.
(7) For a similar preparation of 5b, see: King, J. F.; Loosmore,
S. M.; Aslam, M.; Lock, J. D.; McGarrity, M. J. J. Am.
Chem. Soc. 1982, 104, 7108.
(8) For an alternative preparation of 5f and 5g, see: Visgert, R.
V.; Skrypnik, Y. G. Russ. J. Org. Chem. 1970, 6, 2068.
(9) General Procedure: To an ice-cooled soln of alcohol 4 (1
mmol), DMAP (0.1 mmol) and triethylamine (1.2 mmol) in
CH2Cl2 (10 mL) was added dropwise sulfonyl chloride 3
(1.2 mmol). Stirring was continued at 0 °C for the time
indicated in Table 1. The mixture was washed with cold
water (7.5 mL), 1 N HCl (7.5 mL) and sat. aq NaHCO3 (7.5
mL). After drying the organic layer over MgSO4, the solvent
was evaporated and the residue was subjected to bulb to bulb
distillation to give the pure sulfonate 5. To a stirred soln of
(10) Sultones 6a (see ref.2c and ref.11a), 6f (see ref.11b) and 6g (see
ref.11c) are known compounds.
(11) (a) Bonini, B. F.; Kemperman, G.; Willems, S. T. H.; Fochi,
M.; Mazzanti, G.; Zwanenburg, B. Synlett 1998, 1411.
(b) Moiseenkov, A. M.; Polunin, E. V.; Zaks, I. M. Russ.
Chem. Bull. 1984, 33, 2519. (c) Schonk, R. M.; Bakker, B.
H.; Cerfontain, H. Recl. Trav. Chim. Pays-Bas 1993, 112,
201.
(12) Crystallographic data (excluding structure factors) for the
structure reported in this paper have been deposited with the
Cambridge Crystallographic Data Centre as supplementary
publication no. CCDC-187416. Copies of the data can be
obtained free of charge on application to CCDC, 12 Union
Road, Cambridge CB2 1EZ, UK (fax: +44(1223)336033; e-
mail: deposit@ccdc.cam.ac.uk).
(13) For ring closing metathesis to , -unsaturated lactones using
ruthenium carbene complexes with NHC ligands, see e.g.:
(a) Held, C.; Fröhlich, R.; Metz, P. Adv. Synth. Catal. 2002,
344, 720. (b) Nakashima, K.; Imoto, M.; Miki, T.; Miyake,
T.; Fujisaki, N.; Fukunaga, S.; Mizutani, R.; Sono, M.; Tori,
M. Heterocycles 2002, 56, 85. (c) Lee, C. W.; Grubbs, R. H.
J. Org. Chem. 2001, 66, 7155. (d) Chatterjee, A. K.;
Morgan, J. P.; Scholl, M.; Grubbs, R. H. J. Am. Chem. Soc.
2000, 122, 3783. (e) Fürstner, A.; Thiel, O. R.; Ackermann,
L.; Schanz, H.-J.; Nolan, S. P. J. Org. Chem. 2000, 65, 2204.
Synlett 2002, No. 12, 2019–2022 ISSN 0936-5214 © Thieme Stuttgart · New York