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70449661931
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note
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The methylenated adducts 1, 2, and 13 were stable for at least a month when stored below 0°C. However, prolonged storage resulted in gradual decomposition.
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28
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70449692432
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note
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Gas phase density functional calculations performed at the B3LYP/6-31 +G(d)//B3LYP/6-31+G(d) level support the conclusion that 1 is thermodynamically favored over 6 with a Boltzmann distribution of 98:2 based on unscaled zeropoint corrected electronic energies at 298 K (ΔE=9.78 kJ/mol). See the Supporting Information for computational details.
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Shono, T.; Matsumura, Y.; Onomura, O.; Yamada, Y. Tetrahedron Lett. 1987, 28, 4073-4074.
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33
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0032887207
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The homo- and heterodimerization of enecarbamates has been reported; see ref 3 and
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The homo- and heterodimerization of enecarbamates has been reported; see ref 3 and: Oliveira, D. F.; Miranda, P. C. M. L.; Correia, C. R. D. J. Org. Chem. 1999, 64, 6646-6652.
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Oliveira, D.F.1
Miranda, P.C.M.L.2
Correia, C.R.D.3
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34
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33846986839
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Conventional heating gave significant amounts of starting material 12 and N,O-acetal 9 byproduct. Microwave-assisted organocatalytic Mannich reactions have been described, see
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Conventional heating gave significant amounts of starting material 12 and N,O-acetal 9 byproduct. Microwave-assisted organocatalytic Mannich reactions have been described, see: (a)Hosseini,M.; Stiasni, N.;Barbieri, V.; Kappe, C. O. J. Org. Chem. 2007, 72, 1417-1424.
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0346456942
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36
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39
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70449685109
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note
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The C1′ alkylated adduct of 1 with anisole (cf. adduct 22) is predicted be thermodynamically favored over the C2 adduct by 37.7 kJ/mol based on unscaled zero-point corrected electronic energies at 298 K. See the Experimental Section for computational details.
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40
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0028824251
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N-Acyliminium cyclizations are used extensively for the construction of heterocyclic ring systems; see
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N-Acyliminium cyclizations are used extensively for the construction of heterocyclic ring systems; see: (a) Marson, C. M.; Pink, J. H.; Smith, C. Tetrahedron Lett. 1995, 36, 8107-8110.
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0000860321
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(c) Shono, T.; Matsumura, Y.; Tsubata, K. J. Am. Chem. Soc. 1981, 103, 1172-1176.
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33845283120
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(e) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915.
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45
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33749436403
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The asymmetric hydrogenation of β-acyl enecarbamates has been demonstrated, see
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The asymmetric hydrogenation of β-acyl enecarbamates has been demonstrated, see: Lei, A.; Chen, M.; He, M.; Zhang, X. Eur. J. Org. Chem. 2006, 19, 4343-4347.
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Lei, A.1
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Zhang, X.4
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46
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70449661929
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note
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Dynamic NMR effects due to hindered rotation about the CO-N bond.
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