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(i) Wang, C.-C.; Li, J. J.; Huang, H.-C.; Lee, L. F.; Reitz, D. B. J. Org. Chem. 2000, 65, 2711-2715.
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It is likely that the nitrogen-induced stabilization in the six-membered cyclic lithiated intermediated 1-Li, and Complex Induced Proximity Effect could act sinergically making the lateral benzylic position the kinetically and thermodynamically favored one, see: (a) Pergamon: Oxford, UK, Chapter 2
-
It is likely that the nitrogen-induced stabilization in the six-membered cyclic lithiated intermediated 1-Li, and Complex Induced Proximity Effect could act sinergically making the lateral benzylic position the kinetically and thermodynamically favored one, see: (a) Clayden J., In Organolithiums: Selectivity for Synthesis; Pergamon: Oxford, UK, 2002; Chapter 2.
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For other examples of nitrogen-assisted lithiation see: (a) Ross Kelly, T.; Lebedev, R. L. J. Org. Chem. 2002, 67, 2197-2205.
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70349159807
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note
-
Following a referee's suggestion, the one-pot cyclization was performed by addition of 2 mL of acetic acid to the reaction mixture (1 mmol scale) obtained after quenching of the lithiated intermediate with benzophenone. The complete conversion of 2f into 3b was observed and the isochroman was isolated with 40% yield.
-
-
-
-
39
-
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70349117165
-
-
note
-
This assumption rises considering that the reaction on pure diastereomers of (R*,R*)-2h,i and (R*,S*)-2h,i is highly stereospecific giving only one isochroman. Likely, a mixture of diastereomeric isochromans should have been obtained with an SN1 mechanism.
-
-
-
-
40
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70349156120
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-
note
-
3COOH to the starting aziridine 2.
-
-
-
-
41
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70349159350
-
-
CCDC 733354 contains the supplementary crystallographic data for compound (R*,R*)-2i. These data have been deposited with the Cambridge Crystallographic Data Centre and can be obtained free of charge via
-
CCDC 733354 contains the supplementary crystallographic data for compound (R*,R*)-2i. These data have been deposited with the Cambridge Crystallographic Data Centre and can be obtained free of charge via www. ccdc.cam.ac.uk/data-request/cif.
-
-
-
-
42
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70349108634
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Patent WO 96/38435, 1996
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(a) Schoenleber, R. W.; DeNinno, M. P.; Basha, F. Z.; Ehrlich, P. P.; Perner, R. J.; Meyer, M. D.; Campbell, J. R.; Martin, Y. C.; Stout, D. M.; De Bernardis, J. F.; Morton, H. E.; Michaelides, M. Patent WO 96/38435, 1996.
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25844525707
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44
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(c) TenBrink, R. E.; Bergh, C. L.; Duncan, J. N.; Harris, D.W.; Huff, R. M.; Lahti, R. A.; Lawson, C. F.; Lutzke, B. S.; Martin, I. J.; Rees, S. A.; Schlachter, S. K.; Sih, J. C.; Smith, M.W. J. Med. Chem. 1996, 39, 2435-2437.
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47
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0002994828
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-
The resonance effect is often invoked for this kind of intermediate even if their structures are still unknown, see: (a)
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The resonance effect is often invoked for this kind of intermediate even if their structures are still unknown, see: (a) Clark, R. D.; Jahangir, A. Org. React. 1995, 47, 1-314.
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0020464967
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(b) Ito, Y.; Nakatsuka, M.; Saegusa, T. J. Am. Chem. Soc. 1982, 104, 7609-7622.
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Ito, Y.1
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49
-
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42149123402
-
-
A NMR investigation could help to shed light on this isomerization process; for a related example on the solvent effect, see
-
A NMR investigation could help to shed light on this isomerization process; for a related example on the solvent effect, see: Capriati, V.; Florio, S.; Luisi, R.; Mazzanti, A.; Musio, B. J. Org. Chem. 2008, 73, 3197-3204.
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Capriati, V.1
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Mazzanti, A.4
Musio, B.5
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50
-
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70349090376
-
-
note
-
The absolute configuration could be assigned considering that the intramolecular cyclization is highly stereospecific (see infra).
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