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0013599104
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Permanent address: Department of Chemistry, Faculty of Science at Qena, South Valley University, Qena, Egypt
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Permanent address: Department of Chemistry, Faculty of Science at Qena, South Valley University, Qena, Egypt.
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4
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0002108906
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Padwa, A. Ed.; John Wiley and Sons; New York, Chapter 9
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For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
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(1984)
1,3-Dipolar Cycloaddition Chemistry
, vol.2
, pp. 83-168
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Tufariello, J.J.1
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5
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0000582924
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Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford Ch. 4.10
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For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
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(1991)
Comprehensive Organic Synthesis
, vol.4
, pp. 1111-1168
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Wade, P.A.1
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6
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0031012571
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For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
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(1997)
Tetrahedron
, vol.53
, pp. 403
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Frederickson, M.1
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7
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11544346529
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For reviews on nitrone cycloaddition reaction in organic synthesis, see: a) Tufariello, J.J. In 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; John Wiley and Sons; New York, 1984, Vol. 2; Chapter 9; p. 83-168. b) Wade, P. A. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I; Semmelhack, M. E. Eds.; Pergamon Press, Oxford 1991, Vol. 4, Ch. 4.10, pp. 1111-1168. c) Frederickson, M. Tetrahedron 1997, 53, 403. d) Gothelf, K. V.; Jorgensen, K. A. Chem. Rev. 1998, 98, 863.
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(1998)
Chem. Rev.
, vol.98
, pp. 863
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Gothelf, K.V.1
Jorgensen, K.A.2
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8
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0032171497
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a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 6589
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Alcaide, B.1
Rodríguez-Vicente, A.2
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0032476127
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a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
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(1998)
J. Org. Chem.
, vol.63
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Polanco, C.2
Sierra, M.A.3
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0030590508
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a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
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(1996)
Tetrahedron Lett.
, vol.37
, pp. 6901
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Polanco, C.2
Sierra, M.A.3
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0029822636
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a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
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(1996)
J. Org. Chem.
, vol.61
, pp. 7125
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Alcaide, B.1
Polanco, C.2
Sáez, E.3
Sierra, M.A.4
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0030221457
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a) Alcaide, B.; Rodríguez-Vicente, A Tetrahedron Lett. 1998, 39, 6589. b) Alcaide, B.; Polanco, C.; Sierra, M. A. J. Org. Chem. 1998, 63, 6786. c) Alcaide, B.; Polanco, C.; Sierra, M. A. Tetrahedron Lett. 1996, 37, 6901. d) Alcaide, B.; Polanco, C.; Sáez, E.; Sierra, M. A. J. Org. Chem. 1996, 61, 7125 e) Alcaide, B.; Rodríguez-Vicente, A.; Sierra, M.A. Tetrahedron: Asymmetry 1996, 7, 2203.
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(1996)
Tetrahedron: Asymmetry
, vol.7
, pp. 2203
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Alcaide, B.1
Rodríguez-Vicente, A.2
Sierra, M.A.3
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0002653599
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INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
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(1991)
Synlett.
, pp. 520
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Kang, S.H.1
Kim, W.J.2
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15
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0029117325
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INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
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(1995)
Tetrahedron Lett.
, vol.36
, pp. 6713
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Kang, S.H.1
Lee, H.S.2
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16
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0030037595
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INAC reactions of aliphatic 2-substituted 5-hexenyl and 5-heptenyl nitrones have been successfully used for the synthesis of key monocyclic intermediates of 1β-methylthienamycin. A notable feature of such processes is their propensity for the predominant formation of the fused bicyclic systems as opposed to the bridged systems. See, for example: a) Kang, S. H.; Kim, W. J. Synlett. 1991, 520. b) Kang, S. H.; Lee, H. S. Tetrahedron Lett. 1995, 36, 6713. b) Junk, M. E.;Vu, B. T. J. Org. Chem. 1996, 61, 4427.
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(1996)
J. Org. Chem.
, vol.61
, pp. 4427
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Junk, M.E.1
Vu, B.T.2
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0347866330
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For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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(1981)
J. Chem. Soc., Chem. Commun.
, pp. 946
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Branch, C.L.1
Pearson, M.J.2
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0020614647
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For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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(1983)
Tetrahedron Lett.
, vol.24
, pp. 1649
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Branch, C.L.1
Pearson, M.J.2
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0013622738
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For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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(1981)
Heterocycles
, vol.16
, pp. 1495
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Nagakura, I.1
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0006480104
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For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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(1987)
Tetrahedron Lett.
, vol.28
, pp. 97
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Keshava Murthy, K.S.1
Hassner, A.2
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21
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0001570170
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For other related intramolecular nitrile oxide-olefin and azide-olefin cycloadditions in the β-lactam series see: a) Branch, C. L.; Pearson, M. J. J. Chem. Soc., Chem. Commun. 1981, 946. b) Branch, C. L.; Pearson, M. J. Tetrahedron Lett. 1983, 24, 1649. c) Nagakura, I. Heterocycles 1981, 16, 1495. d) Keshava Murthy, K. S.; Hassner, A. Tetrahedron Lett. 1987, 28, 97. e) Hassner, A.; Keshava Murthy, K. S.; Padwa, A.; Bullock, W. H.; Stull, P. D. J. Org. Chem. 1988, 53, 5063.
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(1988)
J. Org. Chem.
, vol.53
, pp. 5063
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Hassner, A.1
Keshava Murthy, K.S.2
Padwa, A.3
Bullock, W.H.4
Stull, P.D.5
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22
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0030731022
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See, for instance: a) van Boggelen, M. P.; van Dommelen, B. F. G. A.; Jiang, Sh.; Singh, G. Tetrahedron 1997, 53, 16897. b) Tsay, S.-C.; Patel, H. V.; Hwu, J. R. Synlett. 1998, 939.
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(1997)
Tetrahedron
, vol.53
, pp. 16897
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Van Boggelen, M.P.1
Van Dommelen, B.F.G.A.2
Jiang, Sh.3
Singh, G.4
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23
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0001316970
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See, for instance: a) van Boggelen, M. P.; van Dommelen, B. F. G. A.; Jiang, Sh.; Singh, G. Tetrahedron 1997, 53, 16897. b) Tsay, S.-C.; Patel, H. V.; Hwu, J. R. Synlett. 1998, 939.
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(1998)
Synlett.
, pp. 939
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Tsay, S.-C.1
Patel, H.V.2
Hwu, J.R.3
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24
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0001318920
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a) (g) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227. b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Ch. 3, p 295.
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(1988)
J. Org. Chem.
, vol.53
, pp. 4227
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Wagle, D.R.1
Garai, C.2
Chiang, J.3
Monteleone, M.G.4
Kurys, B.E.5
Strohmeyer, T.W.6
Hedge, V.R.7
Manhas, M.S.8
Bose, A.K.9
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0002674759
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Georg, G. I., Ed.; VCH: Weinheim, Ch. 3
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a) (g) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227. b) Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: Weinheim, 1993; Ch. 3, p 295.
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(1993)
The Organic Chemistry of β-Lactams
, pp. 295
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Georg, G.I.1
Ravikumar, V.T.2
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-1; F(000) = 552. A colourless crystal of 0.66×0.16×0.16 mm was used. 1210 independent reflections were collected on four circle Seifert XRD 3000S difractometer. The structure was solved by direct methods (SIR92 and difference Fourier techniques; not absorption correction was applied (m = 0.79 mm-1); all calculations were done with the program SHELX97 on a VAX 6410 computer. The structure was refined using full matrix least-squares procedures. Coordinates have been deposited at the Cambridge Crystallographic Data Centre. Figure. Crystal structure of (-)-3a (equation presented)
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-1; F(000) = 552. A colourless crystal of 0.66×0.16×0.16 mm was used. 1210 independent reflections were collected on four circle Seifert XRD 3000S difractometer. The structure was solved by direct methods (SIR92 and difference Fourier techniques; not absorption correction was applied (m = 0.79 mm-1); all calculations were done with the program SHELX97 on a VAX 6410 computer. The structure was refined using full matrix least-squares procedures. Coordinates have been deposited at the Cambridge Crystallographic Data Centre. Figure. Crystal structure of (-)-3a (equation presented)
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0028942843
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Chiacchio, U.; Casuscelli, F.; Corsaro, A.; Librando, V.; Rescifina, A.; Romeo, R.; Romeo, G. Tetrahedron 1995, 51, 5689. For related oxime-olefin (IOOC) reactions, see: Falb, E.; Bechor, Y.; Nudelman, A.; Hassner, A.; Albeck, A.;Gottlieb, H. E. J. Org. Chem. 1999, 64, 498.
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(1995)
Tetrahedron
, vol.51
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Chiacchio, U.1
Casuscelli, F.2
Corsaro, A.3
Librando, V.4
Rescifina, A.5
Romeo, R.6
Romeo, G.7
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28
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0033593493
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Chiacchio, U.; Casuscelli, F.; Corsaro, A.; Librando, V.; Rescifina, A.; Romeo, R.; Romeo, G. Tetrahedron 1995, 51, 5689. For related oxime-olefin (IOOC) reactions, see: Falb, E.; Bechor, Y.; Nudelman, A.; Hassner, A.; Albeck, A.;Gottlieb, H. E. J. Org. Chem. 1999, 64, 498.
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J. Org. Chem.
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Falb, E.1
Bechor, Y.2
Nudelman, A.3
Hassner, A.4
Albeck, A.5
Gottlieb, H.E.6
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a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodriguez-López, J.; Sierra, M. A. Tetrahedron Lett., 1991, 32, 803. b) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M.A; Monge, A.; Pérez-García, V. J. Org. Chem., 1992, 57, 5921.
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Tetrahedron Lett.
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Sierra, M.A.5
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a) Alcaide, B.; Martín-Cantalejo, Y.; Plumet, J.; Rodriguez-López, J.; Sierra, M. A. Tetrahedron Lett., 1991, 32, 803. b) Alcaide, B.; Martín-Cantalejo, Y.; Pérez-Castells, J.; Rodríguez-López, J.; Sierra, M.A; Monge, A.; Pérez-García, V. J. Org. Chem., 1992, 57, 5921.
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J. Org. Chem.
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Martín-Cantalejo, Y.2
Pérez-Castells, J.3
Rodríguez-López, J.4
Sierra, M.A.5
Monge, A.6
Pérez-García, V.7
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See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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(1976)
J. Org. Chem.
, vol.41
, pp. 855
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House, H.O.1
Manning, D.T.2
Melillo, D.G.3
Lee, L.F.4
Haynes, O.R.5
Wilkes, B.E.6
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32
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0001573394
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See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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(1979)
Tetrahedron Lett.
, pp. 4391
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Oppolzer, W.1
Siles, S.2
Snowden, R.L.3
Bakker, B.H.4
Petrzilka, M.5
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33
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0001415101
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See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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(1990)
J. Org. Chem.
, vol.55
, pp. 3007
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Ciganek, E.1
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See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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(1992)
Tetrahedron
, vol.48
, pp. 6929
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Grigg, R.1
Markandu, J.2
Perrior, T.3
Surendrakumar, S.4
Warnock, W.J.5
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See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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(1995)
J. Org. Chem.
, vol.60
, pp. 5795
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Ciganek, E.1
Read, J.M.2
Calabrese, J.C.3
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36
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0030603121
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See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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(1996)
Tetrahedron
, vol.52
, pp. 11601
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Davison, E.C.1
Forbes, I.T.2
Holmes, A.B.3
Warner, J.A.4
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37
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0030693920
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and other references cited therein
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See, for example: a) House, H. O.; Manning, D. T.; Melillo, D. G.; Lee, L. F.; Haynes, O. R.; Wilkes, B. E. J. Org. Chem., 1976, 41, 855. b) Oppolzer, W.; Siles, S.; Snowden, R. L.; Bakker, B. H.;Petrzilka, M. Tetrahedron Lett. 1979, 4391. c) Ciganek, E. J. Org. Chem. 1990, 55, 3007. d) Grigg, R.; Markandu, J.; Perrior, T.; Surendrakumar, S.; Warnock, W. J. Tetrahedron 1992, 48, 6929. e) Ciganek, E.; Read, J. M.; Calabrese, J. C. J. Org. Chem. 1995, 60, 5795. f) Davison, E. C.; Forbes, I. T.; Holmes, A. B.; Warner, J. A. Tetrahedron 1996, 52, 11601. Coogan, M. P.; Gravestock, M. B.; Knight, D. W.; Thornton, S. R. Tetrahedron Lett. 1997, 38, 8549 and other references cited therein.
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(1997)
Tetrahedron Lett.
, vol.38
, pp. 8549
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Coogan, M.P.1
Gravestock, M.B.2
Knight, D.W.3
Thornton, S.R.4
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38
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0013622773
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The salient features which distinguished between the two regioisomers (2a and 3a, for example) was the presence, in the NMR spectrum of compound 2a, of a highfield one proton multiplet at δ(H) 2.78 coupled to five other protons and a methine carbon signal at δ(C) 37.8 (DEPT), which would be expected for the C-8 methine in the fused structure 2a. Also, this compound showed two methylene carbon resonances at δ(C) 60.8 and 68.6 (DEPT) attributable to two oxygen substituted methylene carbons. Compound 3a displayed a highfield geminally coupled (12.7 Hz) proton signals at δ(H) 2.40 (m) and 1.92 (d), and a methylene carbon resonance at δ(C)28.5 (DEPT), and was consistent with its bridged structure
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The salient features which distinguished between the two regioisomers (2a and 3a, for example) was the presence, in the NMR spectrum of compound 2a, of a highfield one proton multiplet at δ(H) 2.78 coupled to five other protons and a methine carbon signal at δ(C) 37.8 (DEPT), which would be expected for the C-8 methine in the fused structure 2a. Also, this compound showed two methylene carbon resonances at δ(C) 60.8 and 68.6 (DEPT) attributable to two oxygen substituted methylene carbons. Compound 3a displayed a highfield geminally coupled (12.7 Hz) proton signals at δ(H) 2.40 (m) and 1.92 (d), and a methylene carbon resonance at δ(C)28.5 (DEPT), and was consistent with its bridged structure.
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41
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0013571228
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All new compounds gave satisfactory analytical and spectral data
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All new compounds gave satisfactory analytical and spectral data.
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