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Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3633-3643

Highly efficient induction of chirality in intramolecular [2 + 2] cycloadditions between ketenimines and imines

(6) Cossío, Fernando P a Arrieta, Ana a Lecea, Begoña a Alajarín, Mateo b Vidal, Angel b Tovar, Fulgencio b

a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU (Spain)

b UNIVERSITY OF MURCIA (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

IMINE; KETENE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0034674410 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo991826q Document Type: Article

Times cited : (39)

References (68)

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- Ketenimines as two-atom components in [4 + 2] cycloadditions: (a) Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1988, 53, 5501. (b) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379. (c) Molina, P.; Alajarin, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703. (d) Kee-Jung, L.; Heung-Taeck, K.; Boo-Geun, K. J. Heterocycl. Chem. 1997, 34, 1795. Ketenimines as four-atom components in [4 + 2] cycloadditions: (e) Ghosez, L.; de Pérez, C. Angew. Chem., Int. Ed. Engl. 1971, 10, 184. (f) Sonveaux, E.; Ghosez, L. J. Am. Chem. Soc. 1973, 95, 5417. (g) Dondoni, A. Heterocycles 1980, 14, 1547. (h) Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647. (i) Differding, E.; Vandevelde, O.; Roekens, B.; Trieu, T.; Ghosez, L. Tetrahedron Lett. 1987, 28, 397. (j) Molina, P.; López-Leonardo, C. Tetrahedron Lett. 1993, 34, 2809. (k) Molina, P.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1994, 50, 5027. (l) Andrews, I. P.; Bannister, R.; Etridge, S. K.; Lewis, N. J.; Mullane, M. V.; Wells, A. S. Tetrahedron Lett. 1995, 36, 7743. (m) Kee-Jung, L.; Seong-Heon, K.; Jong-Hyuk, K. Synthesis 1997, 1461. (n) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron 1997, 53, 4521. (o) Alajarín, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127. For a review on pericyclic reactions of ketenimines, see: Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. Manuscript in preparation.
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5
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- Ketenimines as two-atom components in [4 + 2] cycloadditions: (a) Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1988, 53, 5501. (b) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379. (c) Molina, P.; Alajarin, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703. (d) Kee-Jung, L.; Heung-Taeck, K.; Boo-Geun, K. J. Heterocycl. Chem. 1997, 34, 1795. Ketenimines as four-atom components in [4 + 2] cycloadditions: (e) Ghosez, L.; de Pérez, C. Angew. Chem., Int. Ed. Engl. 1971, 10, 184. (f) Sonveaux, E.; Ghosez, L. J. Am. Chem. Soc. 1973, 95, 5417. (g) Dondoni, A. Heterocycles 1980, 14, 1547. (h) Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647. (i) Differding, E.; Vandevelde, O.; Roekens, B.; Trieu, T.; Ghosez, L. Tetrahedron Lett. 1987, 28, 397. (j) Molina, P.; López-Leonardo, C. Tetrahedron Lett. 1993, 34, 2809. (k) Molina, P.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1994, 50, 5027. (l) Andrews, I. P.; Bannister, R.; Etridge, S. K.; Lewis, N. J.; Mullane, M. V.; Wells, A. S. Tetrahedron Lett. 1995, 36, 7743. (m) Kee-Jung, L.; Seong-Heon, K.; Jong-Hyuk, K. Synthesis 1997, 1461. (n) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron 1997, 53, 4521. (o) Alajarín, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127. For a review on pericyclic reactions of ketenimines, see: Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. Manuscript in preparation.
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6
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7
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8
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- Ketenimines as two-atom components in [4 + 2] cycloadditions: (a) Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1988, 53, 5501. (b) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379. (c) Molina, P.; Alajarin, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703. (d) Kee-Jung, L.; Heung-Taeck, K.; Boo-Geun, K. J. Heterocycl. Chem. 1997, 34, 1795. Ketenimines as four-atom components in [4 + 2] cycloadditions: (e) Ghosez, L.; de Pérez, C. Angew. Chem., Int. Ed. Engl. 1971, 10, 184. (f) Sonveaux, E.; Ghosez, L. J. Am. Chem. Soc. 1973, 95, 5417. (g) Dondoni, A. Heterocycles 1980, 14, 1547. (h) Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647. (i) Differding, E.; Vandevelde, O.; Roekens, B.; Trieu, T.; Ghosez, L. Tetrahedron Lett. 1987, 28, 397. (j) Molina, P.; López-Leonardo, C. Tetrahedron Lett. 1993, 34, 2809. (k) Molina, P.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1994, 50, 5027. (l) Andrews, I. P.; Bannister, R.; Etridge, S. K.; Lewis, N. J.; Mullane, M. V.; Wells, A. S. Tetrahedron Lett. 1995, 36, 7743. (m) Kee-Jung, L.; Seong-Heon, K.; Jong-Hyuk, K. Synthesis 1997, 1461. (n) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron 1997, 53, 4521. (o) Alajarín, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127. For a review on pericyclic reactions of ketenimines, see: Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. Manuscript in preparation.
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9
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- Ketenimines as two-atom components in [4 + 2] cycloadditions: (a) Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1988, 53, 5501. (b) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379. (c) Molina, P.; Alajarin, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703. (d) Kee-Jung, L.; Heung-Taeck, K.; Boo-Geun, K. J. Heterocycl. Chem. 1997, 34, 1795. Ketenimines as four-atom components in [4 + 2] cycloadditions: (e) Ghosez, L.; de Pérez, C. Angew. Chem., Int. Ed. Engl. 1971, 10, 184. (f) Sonveaux, E.; Ghosez, L. J. Am. Chem. Soc. 1973, 95, 5417. (g) Dondoni, A. Heterocycles 1980, 14, 1547. (h) Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647. (i) Differding, E.; Vandevelde, O.; Roekens, B.; Trieu, T.; Ghosez, L. Tetrahedron Lett. 1987, 28, 397. (j) Molina, P.; López-Leonardo, C. Tetrahedron Lett. 1993, 34, 2809. (k) Molina, P.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1994, 50, 5027. (l) Andrews, I. P.; Bannister, R.; Etridge, S. K.; Lewis, N. J.; Mullane, M. V.; Wells, A. S. Tetrahedron Lett. 1995, 36, 7743. (m) Kee-Jung, L.; Seong-Heon, K.; Jong-Hyuk, K. Synthesis 1997, 1461. (n) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron 1997, 53, 4521. (o) Alajarín, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127. For a review on pericyclic reactions of ketenimines, see: Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. Manuscript in preparation.
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- Ketenimines as two-atom components in [4 + 2] cycloadditions: (a) Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1988, 53, 5501. (b) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379. (c) Molina, P.; Alajarin, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703. (d) Kee-Jung, L.; Heung-Taeck, K.; Boo-Geun, K. J. Heterocycl. Chem. 1997, 34, 1795. Ketenimines as four-atom components in [4 + 2] cycloadditions: (e) Ghosez, L.; de Pérez, C. Angew. Chem., Int. Ed. Engl. 1971, 10, 184. (f) Sonveaux, E.; Ghosez, L. J. Am. Chem. Soc. 1973, 95, 5417. (g) Dondoni, A. Heterocycles 1980, 14, 1547. (h) Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647. (i) Differding, E.; Vandevelde, O.; Roekens, B.; Trieu, T.; Ghosez, L. Tetrahedron Lett. 1987, 28, 397. (j) Molina, P.; López-Leonardo, C. Tetrahedron Lett. 1993, 34, 2809. (k) Molina, P.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1994, 50, 5027. (l) Andrews, I. P.; Bannister, R.; Etridge, S. K.; Lewis, N. J.; Mullane, M. V.; Wells, A. S. Tetrahedron Lett. 1995, 36, 7743. (m) Kee-Jung, L.; Seong-Heon, K.; Jong-Hyuk, K. Synthesis 1997, 1461. (n) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron 1997, 53, 4521. (o) Alajarín, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127. For a review on pericyclic reactions of ketenimines, see: Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. Manuscript in preparation.
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- Molina, P.¹ López-Leonardo, C.²

11
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- Ketenimines as two-atom components in [4 + 2] cycloadditions: (a) Barbaro, G.; Battaglia, A.; Giorgianni, P. J. Org. Chem. 1988, 53, 5501. (b) Molina, P.; Alajarin, M.; Vidal, A. Tetrahedron Lett. 1991, 32, 5379. (c) Molina, P.; Alajarin, M.; Vidal, A. J. Org. Chem. 1992, 57, 6703. (d) Kee-Jung, L.; Heung-Taeck, K.; Boo-Geun, K. J. Heterocycl. Chem. 1997, 34, 1795. Ketenimines as four-atom components in [4 + 2] cycloadditions: (e) Ghosez, L.; de Pérez, C. Angew. Chem., Int. Ed. Engl. 1971, 10, 184. (f) Sonveaux, E.; Ghosez, L. J. Am. Chem. Soc. 1973, 95, 5417. (g) Dondoni, A. Heterocycles 1980, 14, 1547. (h) Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647. (i) Differding, E.; Vandevelde, O.; Roekens, B.; Trieu, T.; Ghosez, L. Tetrahedron Lett. 1987, 28, 397. (j) Molina, P.; López-Leonardo, C. Tetrahedron Lett. 1993, 34, 2809. (k) Molina, P.; López-Leonardo, C.; Alcántara, J. Tetrahedron 1994, 50, 5027. (l) Andrews, I. P.; Bannister, R.; Etridge, S. K.; Lewis, N. J.; Mullane, M. V.; Wells, A. S. Tetrahedron Lett. 1995, 36, 7743. (m) Kee-Jung, L.; Seong-Heon, K.; Jong-Hyuk, K. Synthesis 1997, 1461. (n) Barluenga, J.; Ferrero, M.; Palacios, F. Tetrahedron 1997, 53, 4521. (o) Alajarín, M.; Vidal, A.; Tovar, F.; Conesa, C. Tetrahedron Lett. 1999, 40, 6127. For a review on pericyclic reactions of ketenimines, see: Alajarín, M.; Vidal, A.; Tovar, F. Targets Heterocycl. Syst. Manuscript in preparation.
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