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38
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37049067084
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The Z configuration of C=N bond in nitrones 3 and 7 was established by n.O.e. experiments and by the appearance of azomethine proton at 6.8 ppm; in E configurated aldonitrones the azomethine proton is found downfield at 8.0-8.5 ppm; see Sivasubramanian, S.; Mohan, P.; Thirumalaikumar, M.; Muthusubramanian, S. J. Chem. Soc. Perkin Trans. 1 1994, 3353.
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The use of THF as solvent has been reported to give somewhat lower diastereoselectivities compared to ether and dichloromethane: see (a) Chang, Z.-Y; Coates, R. M. J. Org. Chem. 1990, 55, 3464;
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41
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0343970547
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note
-
Our efforts to carry out the reaction at - 10°C and below in diethylether and dichloromethane and below - 30°C in THF failed due to the insolubility of the nitrones.
-
-
-
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42
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0029994555
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The effect of various Lewis acids on the stereochemical course of 1,3-addition reactions of 2-trimethylsilyloxyfuran to nitrones has been recently reported by us: Castellari, C.; Lombarde, M.; Pietropaolo, G.; Trombini, C. Tetrahedron: Asymmetry 1996, 7, 1059.
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43
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0029928097
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Very interesting inversions of diastereoselectivity in 1,3-addition reactions of lithium derivatives to nitrones in the presence of Lewis acids have been recently reported: (a) Merchan, F. L.; Merino, P.; Rojo, I.; Tejero, T.; Dondoni, A. Tetrahedron: Asymmetry 1996, 7, 667;
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Houck, K. N.; Paddon-Row, N. M.; Rondan, N. G.; Wu, Y. D.; Brown, F. K.; Spellmeyer, D. C.; Metz, J. T.; Li, Y.; Loncharich, R. J. Science 1986, 231, 1108.
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Inouye, S.; Tsuruoka, T.; Ito, T.; Niida, T. Tetrahedron 1968, 23, 2125.
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61
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0343970523
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University of Gottingen, Germany
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(b) Sheldrick, G. M. (1993), University of Gottingen, Germany.
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(1993)
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Sheldrick, G.M.1
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62
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0343534622
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note
-
Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Data Centre.
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63
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0027994561
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Dondoni, A.; Franco, S.; Junquera, F.; Merchan, F.; Merino, P.; Tejero, T. Synth. Commun. 1994, 24, 2537.
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Tejero, T.6
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64
-
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0343098719
-
-
note
-
3 protons in the region 1.35-1.66 ppm.
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-
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