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33750822554
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Khlebnikov, A.F.1
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Kostikov, R.R.3
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2
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0346265937
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Hegedus, L. S., Ed.; Pergamon Press: New York, Chapter 5.2
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Reviews: (a) Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Adv. Heterocycl. Chem. 1996, 65, 93. (b) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (f) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. (g) Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 4.2. (h) Doyle, M. P. Chem. Rev. 1986, 86, 919.
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Reviews: (a) Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Adv. Heterocycl. Chem. 1996, 65, 93. (b) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (f) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. (g) Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 4.2. (h) Doyle, M. P. Chem. Rev. 1986, 86, 919.
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Adams, J.1
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7
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Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, Chapter 4.2
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Reviews: (a) Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Adv. Heterocycl. Chem. 1996, 65, 93. (b) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (f) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. (g) Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 4.2. (h) Doyle, M. P. Chem. Rev. 1986, 86, 919.
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Taber, D.F.1
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8
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Reviews: (a) Khlebnikov, A. F.; Novikov, M. S.; Kostikov, R. R. Adv. Heterocycl. Chem. 1996, 65, 93. (b) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (e) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (f) Adams, J.; Spero, D. M. Tetrahedron 1991, 47, 1765. (g) Taber, D. F. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, Chapter 4.2. (h) Doyle, M. P. Chem. Rev. 1986, 86, 919.
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0028942288
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and references therein
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Selected examples of homochiral Rh(II) complexes used in intramolecular C-H insertion: Rh(II) Carboxylates: (a) Watanabe, N.; Ohtake, Y.; Hashimoto, S.-I.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491 and references therein. (b) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 2725.
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Selected examples of homochiral Rh(II) complexes used in intramolecular C-H insertion: Rh(II) Carboxylates: (a) Watanabe, N.; Ohtake, Y.; Hashimoto, S.-I.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491 and references therein. (b) Sawamura, M.; Sasaki, H.; Nakata, T.; Ito, Y. Bull. Chem. Soc. Jpn. 1993, 66, 2725.
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Sawamura, M.1
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(c) McKervey, M. A.; Ye, T. Chem. Commun. 1992, 823 and references cited. Rh(II) "Carboxamides":
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(d) Doyle, M. P.; Winchester, W. B.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosch, R. J. Am. Chem. Soc. 1993, 115, 9968.
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(e) Doyle, M. P.; Protopopova, M. N.; Winchester, W. R.; Daniel, K. L. Tetrahedron Lett. 1992, 33, 7819.
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20
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0001356018
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and references cited. Rh(II) Phosphate
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(f) Doyle, M. P.; Protopopova, M. N.; Zhou, Q.-L.; Bode, J. W.; Simonsen, S. H.; Lynch, V. J. Org. Chem. 1995, 60, 6654 and references cited. Rh(II) Phosphate:
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Doyle, M.P.1
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21
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(g) McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983.
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For example: (a) Pyrrolizidine alkaloid: Doyle, M. P.; Kalinin, A. V. Tetrahedron Lett. 1996, 37, 1371. (b) Lignan lactones: Bode, J. W.; Doyle, M. P.; Protopova, M. N.; Zhou, Q.-L. J. Org. Chem. 1996, 61, 9146.
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Doyle, M.P.1
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For example: (a) Pyrrolizidine alkaloid: Doyle, M. P.; Kalinin, A. V. Tetrahedron Lett. 1996, 37, 1371. (b) Lignan lactones: Bode, J. W.; Doyle, M. P.; Protopova, M. N.; Zhou, Q.-L. J. Org. Chem. 1996, 61, 9146.
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2, 1:10 v/v) groups.
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note
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(c) The carboxylic acids were either prepared using standard chemical transformations (e.g., hydrolysis of nitriles; oxidation of primary alcohols) or were commercially available.
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(a) See the Supporting Information.
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43
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Hiemstra, H.1
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33751500380
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and references therein
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6 that 2-pyrrolidinone products are usually favored, we felt that it was necessary to reevaluate the regioselectivity in these systems because it is well-known that structural changes in the diazo substrate can have a significant influence on the regioselectivity of the reaction. For example, see Doyle, M. P.; Pieters, R. J.; Taunton, J.; Pho, H. Q.; Padwa, A.; Hertzog, D. L.; Precedo, L. J. Org. Chem. 1991, 56, 820 and references therein.
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Winchester, W.R.7
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53
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85088545312
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note
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26b
-
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54
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1542491729
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note
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(b) When dry benzene was used, TLC analysis of the reaction mixture showed that the reaction was not as "clean".
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55
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(a) Brown, D. S.; Elliot, M. C.; Moody, C. J.; Mowlem, T. J.; Marino, J. P., Jr.; Padwa, A. J. Org. Chem. 1994, 59, 2447.
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(a) Krapcho, A. P. Synthesis 1982, 805 and 893. For other decarboxylation methods, see: Meyers, A. I.; Snyder, L. J. Org. Chem. 1992, 57, 3814 and references therein.
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(a) Krapcho, A. P. Synthesis 1982, 805 and 893. For other decarboxylation methods, see: Meyers, A. I.; Snyder, L. J. Org. Chem. 1992, 57, 3814 and references therein.
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For a discussion on the dramatic influence of solvent polarity on the chemoselectivity of the Rh(II)-carbenoid mediated reaction, see: Davies, H. M. L.; Matasi, J. J.; Ahmed, G. J. Org. Chem. 1996, 61, 2305 and references therein.
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