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77949290946
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2NEt, DBU, and tetramethylguanidine in various solvents resulted in unsatisfactory results.
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2NEt, DBU, and tetramethylguanidine in various solvents resulted in unsatisfactory results.
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77949292821
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2 to enhance the selectivity of the formation of nitro styrenes has not been reported.
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39
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77949301192
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For an improved, practical preparation of DMQ without chromatographic purification, see the Supporting Information
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For an improved, practical preparation of DMQ without chromatographic purification, see the Supporting Information.
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22244444458
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77949293007
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For an alternative synthesis as well as optimization of the cascade reaction using 4-methoxybenzyl amine, see the Supporting Information.
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For an alternative synthesis as well as optimization of the cascade reaction using 4-methoxybenzyl amine, see the Supporting Information.
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49
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34547623795
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3, see: Zacuto, M. J.; Xu, F. J. Org. Chem. 2007, 72, 6298-6300. However, deprotection of N-allyl lactams as described here gave a mixture of deprotected lactam 17 and N,O-acetal lactam. 18.
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3, see: Zacuto, M. J.; Xu, F. J. Org. Chem. 2007, 72, 6298-6300. However, deprotection of N-allyl lactams as described here gave a mixture of deprotected lactam 17 and N,O-acetal lactam. 18.
-
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50
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77949293979
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-
Presumably due to the less nucleophilic aryl amine nitrogen, the cascade coupling stalled at intermediate 1.3 when aryl amines such as 4-methoxyphenylamine were used. The formation of 13a thus further supports the stepwise reaction pathway (Scheme 3). Chemical Equetion Presentation
-
Presumably due to the less nucleophilic aryl amine nitrogen, the cascade coupling stalled at intermediate 1.3 when aryl amines such as 4-methoxyphenylamine were used. The formation of 13a thus further supports the stepwise reaction pathway (Scheme 3). Chemical Equetion Presentation
-
-
-
-
51
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77949310933
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-
It is not very clear why the cis isomer is the major product through acidic equilibrium. Presumably, the formation of the cis isomer is kinetically favored under acidic conditions.
-
It is not very clear why the cis isomer is the major product through acidic equilibrium. Presumably, the formation of the cis isomer is kinetically favored under acidic conditions.
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52
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77949285631
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Attempts to hydrolyze 19 under acidic conditions resulted in epimerization of the stereogenic center adjacent to nitro group, to the undesired corresponding n-propyl lactam
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Attempts to hydrolyze 19 under acidic conditions resulted in epimerization of the stereogenic center adjacent to nitro group. In addition, subsequent hydrogenation would also reduce enamine 19 to the undesired corresponding n-propyl lactam.
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In addition, subsequent hydrogenation would also reduce enamine
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Su, A. C. Adv. Organomet. Chem. 1979, 17, 269. These mechanistic studies, including deuterium labeling experiments, suggest a Rh(I) hydride species is likely the active catalyst, since Rh(III) is reduced to Rh(I) in the presence of olefins and alcohol solvents.
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d) Su, A. C. Adv. Organomet. Chem. 1979, 17, 269. These mechanistic studies, including deuterium labeling experiments, suggest a Rh(I) hydride species is likely the active catalyst, since Rh(III) is reduced to Rh(I) in the presence of olefins and alcohol solvents.
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69
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77949299943
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3 with alcohol solvents was also observed in our previous communication, cf. ref 24.
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3 with alcohol solvents was also observed in our previous communication, cf. ref 24.
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70
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13844251960
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For examples of intramolecular transamidation, see: (a) Tanaka, K.-I, Nemoto, H, Sawanishi, H. Tetrahedron: Asymmetry 2005, 16, 809-815
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For examples of intramolecular transamidation, see: (a) Tanaka, K.-I.; Nemoto, H.; Sawanishi, H. Tetrahedron: Asymmetry 2005, 16, 809-815.
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73
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77949276793
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Although isolation of 24 and 26 from the reaction mixture was difficult, their structures could be unambiguously characterized by applying NMR techniques
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Although isolation of 24 and 26 from the reaction mixture was difficult, their structures could be unambiguously characterized by applying NMR techniques.
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75
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40949153940
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and references cited therein
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b) Tjosaas, F.; Kjerstad, I. B.; Fiksdahl, A. J. Heterocycl. Chem. 2008, 45, 559-562 and references cited therein.
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(2008)
J. Heterocycl. Chem
, vol.45
, pp. 559-562
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Tjosaas, F.1
Kjerstad, I.B.2
Fiksdahl, A.3
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76
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77949299088
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For this specific compound, the sample concentration would also affect the observed chemical shifts
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For this specific compound, the sample concentration would also affect the observed chemical shifts.
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