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concentrated under reduced pressure, and the crude product
was puried by silica gel chromatography (ethyl aceta-
te : hexane ¼ 2 : 3) to afford 2 (12 mg, 92%) as a colorless liquid.
[a]2D5 ꢀ139 (c 1.2, CHCl3); IR (neat): 3458, 2950, 2924, 2854, 1729,
(e) J. A. Love, in Handbook of Metathesis, ed. R. H. Grubbs,
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¨
18; (g) A. Furstner, Angew. Chem., Int. Ed., 2000, 39, 3012;
1
1219 cmꢀ1; H NMR (300 MHz, CDCl3): 5.72 (ddd, J ¼ 2.0, 7.9,
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R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; (j)
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11.9 Hz, 1H), 5.47 (ddd, J ¼ 1.0, 5.9, 10.9 Hz, 1H), 5.31 (ddq, J ¼
1.0, 5.9, 11.9 Hz, 1H), 4.88 (m, 1H), 3.48 (m, 1H), 3.03 (dt, J ¼ 3.9,
10.9 Hz, 1H), 2.68 (dd, J ¼ 3.9, 10.9 Hz, 1H), 2.45 (t, J ¼ 10.9 Hz,
1H), 2.21 (dd, J ¼ 2.0, 13.9 Hz, 1H), 1.32 (d, J ¼ 6.0 Hz, 3H), 1.26
(s, 1H); 13C NMR (75 MHz, CDCl3): 170.0, 135.7, 127.9, 67.8,
67.7, 57.1, 53.4, 43.5, 38.0, 20.4; HRMS (ESI) m/z calcd for
C
10H15O4: [M + H]+ 199.0964, found 199.0965.
Acknowledgements
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D.K.M. thanks CSIR, New Delhi, for nancial support as part of
XII Five Year Plan Programme under title ORIGIN (CSC-0108).
The authors thank Dr G. N. Sastry for helpful discussions on
DFT studies. G.U. thanks the University Grants Commission
(UGC), New Delhi, India, and M.M.R. thanks the Council of
Scientic and Industrial Research (CSIR), New Delhi, India, for
nancial assistance in the form of a research fellowship.
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8340 | RSC Adv., 2014, 4, 8335–8340
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