426
M. Ito et al. / Tetrahedron Letters 42 (2001) 423–427
other 1,4-products 2b–e successfully. Regarding 1,2-re-
gioisomers, the trans stereochemistry for 3a–c was de-
mamoto, Y. J. Am. Chem. Soc. 1989, 111, 4864–4872; (e)
Kang, S.-K.; Lee, D.-H.; Sim, H.-S.; Lim, J.-S. Tetra-
hedron Lett. 1993, 34, 91–94.
1
termined by comparison of the H NMR spectra of the
corresponding saturated alcohols (synthesized by hy-
drogenation) with those of the authentic compounds
prepared by another method.17 The same (trans) stereo-
chemistry was assigned for 3d and 3e by analogy.18–20
11. The cis isomers corresponding to 2a and 3a were pre-
pared by the Mitsunobu reaction.
12. (a) Marino, J. P.; Ferna´ndez de la Pradilla, R.; Laborde,
E. J. Org. Chem. 1987, 52, 4898–4913; (b) Lipshutz, B.
H.; Woo, K.; Gross, T.; Buzard, D. J.; Tirado, R. Synlett
1997, 477–478.
13. (a) Partridge, J. J.; Chadha, N. K.; Uskokovic, M. R. J.
Am. Chem. Soc. 1973, 95, 532–540; (b) Grethe, G.;
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Acknowledgements
This work was supported by a Grant-in-Aid for Scien-
tific Research from the Ministry of Education, Science,
Sports, and Culture Government of Japan.
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Reaction
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Cu(CN)(MgCl) (Table 1, entry 1): To a slurry of CuCN
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1
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1
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OH
O
RT
–18 ~ –10 °C
ii
THF
i
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