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85038551852
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note
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(i) Attempts to improve the stereocontrol were made, however, changing the temperature of lithiation, the use of more bulky bases such as lithium tetramethylpiperidide, or the use of toluene as solvent produced little or no changes of diastereoselectivity.
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22
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85038540810
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note
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(j) This is in agreement with the few existing reports on additions of metallated alkyl sulfoxides across the C-N double bonds of imines (see above, Refs. 5a-h), but in sharp contrast with the peculiar behaviour of α-lithium benzyl p-tolyl sulfoxide, which was found to react with the imine 2 almost exclusively via the syn-geometry (Ref. 3).
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24
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85038551818
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note
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s)-stereochemistry. (figure presented)
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25
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85038554481
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note
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2-3=3.6 Hz strongly suggests a trans pseudo-equatorial configuration, in full agreement with the expected configuration.
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26
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0001621168
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(a) Volonterio, A.; Zanda, M.; Bravo, P.; Fronza, G.; Cavicchio, G.; Crucianelli, M. J. Org. Chem. 1997, 62, 8031-8040.
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(b) Volonterio, A.; Bravo, P.; Capelli, S.; Meille, S. V.; Zanda, M. Tetrahedron Lett. 1997, 38, 1847-1850.
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0345310269
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in press
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(c) Volonterio, A.; Vergani, B.; Crucianelli, M.; Zanda, M.; Bravo, P. J. Org. Chem. 1998, in press.
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29
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85038546266
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note
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4/pyridine is an efficient strategy for obtaining the corresponding desulfenylated derivatives, like 16, with syn-stereoselectivity: see Ref. 8c.
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30
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(a) Chérest, M.; Felkin, H.; Prudent, N. Tetrahedron Lett. 1968, 9, 2199-2202.
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The stereo selectivity of this reaction is quite surprising, since all the reactions of (R)-11 with alkyl, vinyl and phenyl Grignard reagents showed opposite stereocontrol, producing the corresponding anti-products, possibly originated from a highly effective 'chelation control' (Ref. 8b,c). An opposite stereochemical outcome (chelation control) was also reported for a wide range of reactions between N-monoprotected α-amino aldehydes and Grignard reagents, including allylic ones. See for example: (a) Devant, R. M.; Radunz, H.-E. In Houben-Weyl: Methods in Organic Synthesis; Müller, E., Ed.; Thieme Verlag: Stuttgart, 1995; Vol. E21b, pp. 1236-1239.
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(c) Roush, W. R. In Comprehensive Organic Synthesis Vol. 2; Heathcock, C. H., Ed.; Pergamon Press: Oxford, 1991; pp. 1-54.
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Roush, W.R.1
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For recent examples see
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(d) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207-2293. For recent examples see:
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43
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85038550046
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note
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13C NMR, mass spectrometry and microanalyses.
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