Catalysis Science & Technology
Page 8 of 9
ARTICLE
DOI: 10.1039/C4CY00891J
thank Curt Reimann for his support in preparing this 7. A. Dondoni and A. Massi, Angewandte Chemie - International
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Notes and references
Department of Organic Chemistry, Biochemistry and Catalysis, Faculty
of Chemistry, University of Bucharest, Bdul Regina Elisabeta, 4ꢀ12,
Bucharest 030018, Romania. Corresponding authors, eꢀmails:
vasile.parvulescu@g.unibuc.ro; simona.coman@g.unibuc.ro
10. A. Gentile, C. Giordano, C. Fuganti, L. Ghirotto and S. Servi, Journal
of Organic Chemistry, 1992, 57, 6635.
†
All the spectroscopic data for synthesized organic molecules (e.g., 11. L. Protesescu, M. Tudorache, S. Neatu, M. N. Grecu, E. Kemnitz, P.
chiral ketone 3, deketalized chiral ketone
4
and diacetate chiral ketone
5
)
Filip, V. I. Parvulescu and S. M. Coman, Journal of Physical
Chemistry C, 2011, 115, 1112.
and [BMIM][OH] ionic liquid were in accordance with those previously
reported in the literature,27, 60, 64 as follows:
12. N. Candu, M. Tudorache, M. Florea, E. Ilyes, F. Vasiliu, I. Mercioniu,
S. M. Coman, I. Haiduc, M. Andruh and V. I. Pârvulescu,
ChemPlusChem, 2013, 78, 443.
Chiral ketone
(ppm): 1.38 (s, 6Hꢀ CH3ꢀ(1,2ꢀOꢀisopropylidene), CH3ꢀ(4,5ꢀOꢀ
3: δ
1H NMR (Bruker Fourier 300Mz, CDCl3, TMS)
isopropylidene)), 1.44 (s, 3H ꢀCH3ꢀ(1,2ꢀOꢀisopropylidene)), 1.53 (s, 3Hꢀ 13. Y. Tu, Z. X. Wang and Y. Shi, Journal of the American Chemical
CH3ꢀ(4,5ꢀOꢀisopropylidene)), 3.97 (d, J = 9.53 Hz, lH), 4.11 (d, J = 13.6 Society, 1996, 118, 9806.
Hz, 1H), 4.37 (dd, J = 13.6 Hz, J = 2.3 Hz, 1H), 4.53 (ddd, J = 5.6Hz, J = 14. G. A. Cao, Z. X. Wang, Y. Tu and Y. Shi, Tetrahedron Letters, 1998,
2.3 Hz, J = 0.9 Hz, 1H), 4.59 (d, J = 9.53 Hz, 1H), 4.71 (d, J = 5.6 Hz; 39, 4425.
1H). DRIFT spectra
3469 cmꢀ1 (νOH), 2994 cmꢀ1 (νCꢀH), 2939ꢀ2892 15. M. Frohn, M. Dalkiewicz, Y. Tu, Z. X. Wang and Y. Shi, Journal of
cmꢀ1 (νsimCH, νasimCH), 1754 cmꢀ1 (νC=O (ketone)), 1458 cmꢀ1 (δCH of
Organic Chemistry, 1998, 63, 2948.
bonds ꢀCH3 si ꢀCH2), 1388 cmꢀ1 (δCꢀH (methyl)), 1246 cmꢀ1 (CꢀO, νCꢀO), 16. J. C. Lorenz, M. Frohn, X. Zhou, J. R. Zhang, Y. Tang, C. Burke and
:
675ꢀ900 cmꢀ1 (δCꢀH).
Y. Shi, Journal of Organic Chemistry, 2005, 70, 2904.
1H NMR (Bruker Fourier 300Mz, CDCl3) 17. L. Shu and Y. Shi, Tetrahedron Letters, 1999, 40, 8721.
Deketalized chiral ketone
4
:
δ
(ppm): 1.38 (s, 3H), 1.54 (s, 3H), 3.98 (dd, J = 12.78 Hz, J = 2.11 Hz, 18. L. Shu and Y. Shi, Journal of Organic Chemistry, 2000, 65, 8807.
lH), 4.00 (d, J = 9.46 Hz, lH), 4.30 (dd, J = 12.78 Hz, J = 1.3 Hz, lH), 4.39 19. L. Shu and Y. Shi, Tetrahedron, 2001, 57, 5213.
(m, 1H), 4.67 (d, J = 9.46 Hz, 1H), 4.73 (d, J = 3.98 Hz, 1H). DRIFT 20. B. Wang, O. A. Wong, M. X. Zhao and Y. Shi, Journal of Organic
spectra: 3469 and 3401 cmꢀ1 (free OH stretching, νOH), 2901ꢀ2997 cmꢀ1
(νsimCH, νasimCH), 1754 cmꢀ1 (νC=O (ketone)), 1458 cmꢀ1 (δCH of bonds ꢀ 21. Z. X. Wang, G. A. Cao and Y. Shi, Journal of Organic Chemistry
Chemistry, 2008, 73, 9539.
,
CH3 si ꢀCH2), 1388 cmꢀ1 (δCꢀH (methyl)), 1246 cmꢀ1 (CꢀO, νCꢀO), 675ꢀ
900 cmꢀ1 (δCꢀH).
1999, 64, 7646.
22. Z. X. Wang and Y. Shi, Journal of Organic Chemistry, 1998, 63
,
Chiral ketone
5:
1H NMR (Bruker Fourier 300 MHz, CDCl3)
δ
(ppm)
:
3099.
1.39 (s, 3HꢀCH3ꢀ(1,2ꢀOꢀisopropylidene)), 1.54 (s, 3HꢀCH3ꢀ(1,2ꢀOꢀ 23. Z. X. Wang, Y. Tu, M. Frohn and Y. Shi, Journal of Organic
isopropylidene)), 2.11 (s, 3Hꢀ(ꢀOCOCH3)), 2.16 (s, 3Hꢀ(ꢀOCOCH3)), Chemistry, 1997, 62, 2328.
3.94 (dd, J = 13.42 Hz, J = 2.42 Hz, lH), 3.98 (d, J =9.50 Hz, lH), 4.42 24. J. D. Warren and Y. Shi, Journal of Organic Chemistry, 1999, 64
(dd, J = 13.42 Hz, J = 1.13 Hz, lH), 5.60 (m, 1Hꢀ5), 4.67 (d, J = 9.46 Hz, 7675.
1H), 5.88 (d, J = 4.07 Hz, 1H). DRIFT spectra: 3469 cmꢀ1 (νOH), 2901ꢀ 25. Y. Zhu, L. Shu, Y. Tu and Y. Shi, Journal of Organic Chemistry
2997 cmꢀ1 (νsimCH, νasimCH), 1754 cmꢀ1 (νC=O (ketone)), 1458 cmꢀ1 (δCH
2001, 66, 1818.
of bonds ꢀCH3 si ꢀCH2), 1388 cmꢀ1 (δCꢀH (methyl)), 1246 cmꢀ1 (CꢀO, νCꢀ 26. Y. Zhu, Y. Tu, H. Yu and Y. Shi, Tetrahedron Letters, 1998, 39
O), 675ꢀ900 cmꢀ1 (δCꢀH).
7819.
[BMIM][OH] ionic liquid: 1H NMR (Bruker Fourier 300 MHz, CDCl3) 27. X. Peng, P. Li and Y. Shi, Journal of Organic Chemistry, 2012, 77
(ppm): 0.83 (t, J = 7.4 Hz, 3H), 1.12−1.32 (m, 2H), 1.67−1.96 (m, 2H), 701.
2.53 (bs, 1H), 4.00 (s, 3H), 4.22 (t, J = 7.4, 2H), 7.48 (d, J = 1.5 Hz, 1H), 28. B. Wang, X. Y. Wu, O. A. Wong, B. Nettles, M. X. Zhao, D. Chen
,
,
,
,
δ
7.67 (d, J = 1.5 Hz, 1H), 10.19 (s, 1H). DRIFT spectra (neat): 3300,
2915, 2900, 2812, 1650, 1115 cmꢀ1.
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29. X. Y. Wu, X. She and Y. Shi, Journal of the American Chemical
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8 | J. Name., 2012, 00, 1-3
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