Studies of Diastereoselectivity in Conjugate Addition of Organoaluminum Reagents to (R)-[(p-Tolylsulfinyl)methyl]quinols and Derivatives

Journal of Organic Chemistry

Volumn 63, Issue 11, 1998, Pages 3687-3693

  Carreno, M Carmen ^a   González, Manuel Pérez ^a   Ribagorda, María ^a   Houk, K N ^b  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001656341     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980084i     Document Type: Article

References (28)

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2. Reviews: (a) Schmalz, H. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1092, 92, 771. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992, For recent references, see: (d) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971-86. (e) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe. G. Synthesis 1995, 659-66. (f) Lassaletta, J. M.; Fernández, R.; Martín Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002-3.
3. Reviews: (a) Schmalz, H. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1092, 92, 771. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992, For recent references, see: (d) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971-86. (e) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe. G. Synthesis 1995, 659-66. (f) Lassaletta, J. M.; Fernández, R.; Martín Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002-3.
4. Reviews: (a) Schmalz, H. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1092, 92, 771. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992, For recent references, see: (d) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971-86. (e) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe. G. Synthesis 1995, 659-66. (f) Lassaletta, J. M.; Fernández, R.; Martín Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002-3.
5. Reviews: (a) Schmalz, H. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1092, 92, 771. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992, For recent references, see: (d) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971-86. (e) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe. G. Synthesis 1995, 659-66. (f) Lassaletta, J. M.; Fernández, R.; Martín Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002-3.
6. Reviews: (a) Schmalz, H. G. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 1.5. (b) Rossiter, B. E.; Swingle, N. M. Chem. Rev. 1092, 92, 771. (c) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992, For recent references, see: (d) Urban, E.; Knühl, G.; Helmchen, G. Tetrahedron 1996, 52, 971-86. (e) Enders, D.; Kirchhoff, J.; Mannes, D.; Raabe. G. Synthesis 1995, 659-66. (f) Lassaletta, J. M.; Fernández, R.; Martín Zamora, E.; Díez, E. J. Am. Chem. Soc. 1996, 118, 7002-3.
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9. (a) Review: Hua, H. D. in Advances in Carbanion Chemistry; Snieckus, V., Eds.; JAI Press: London, 1992; p 249. (b) Haynes, R. K.; Katsifis, A. G.; Vowiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423-33. (c) Marco, J. L.; Fernández, L; Khiar, N.; Fernández, P.; Romero, A. J. Org. Chem. 1995, 60, 6678-9. (d) Marco, J. L. J. Org. Chem. 1997, 62, 6575-81.
10. (a) Review: Hua, H. D. in Advances in Carbanion Chemistry; Snieckus, V., Eds.; JAI Press: London, 1992; p 249. (b) Haynes, R. K.; Katsifis, A. G.; Vowiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423-33. (c) Marco, J. L.; Fernández, L; Khiar, N.; Fernández, P.; Romero, A. J. Org. Chem. 1995, 60, 6678-9. (d) Marco, J. L. J. Org. Chem. 1997, 62, 6575-81.
11. (a) Review: Hua, H. D. in Advances in Carbanion Chemistry; Snieckus, V., Eds.; JAI Press: London, 1992; p 249. (b) Haynes, R. K.; Katsifis, A. G.; Vowiller, S. C.; Hambley, T. W. J. Am. Chem. Soc. 1988, 110, 5423-33. (c) Marco, J. L.; Fernández, L; Khiar, N.; Fernández, P.; Romero, A. J. Org. Chem. 1995, 60, 6678-9. (d) Marco, J. L. J. Org. Chem. 1997, 62, 6575-81.
12. For an overview of our work see: Carren∼o, M. C. Chem. Rev. 1995, 95, 1717-60.
13. For more recent references see: (a) Bueno, A. B.; Carren∼o, M. C.; García Ruano, J. L.; Gómez Arrayás, R.; Zarzuelo, M. M. J. Org. Chem. 1997, 62, 2139-43. (b) Carren∼o, M. C.; García Ruano, J. L.; Urbano, A.; Lopez Solera, M. I. J. Org. Chem. 1997, 62, 976-81.
14. For more recent references see: (a) Bueno, A. B.; Carren∼o, M. C.; García Ruano, J. L.; Gómez Arrayás, R.; Zarzuelo, M. M. J. Org. Chem. 1997, 62, 2139-43. (b) Carren∼o, M. C.; García Ruano, J. L.; Urbano, A.; Lopez Solera, M. I. J. Org. Chem. 1997, 62, 976-81.
15. Carreno, M. C.; Pérez González, M.; Ribagorda, M.; Fischer, J. J. Org. Chem. 1996, 61, 6758-9.
16. A high π-facial diastereoselectivity was also observed in DielsAlder cycloadditions of 1: (a) Carreno, M. C.; Pérez Gonzalez, M.; Fischer, J. Tetrahedron Lett. 1995, 36, 4893-6. (b) Carren∼o, M. C.; Pérez González, M.; Houk, K. N. J. Org. Chem. 1997, 62, 9128-37.
17. A high π-facial diastereoselectivity was also observed in DielsAlder cycloadditions of 1: (a) Carreno, M. C.; Pérez Gonzalez, M.; Fischer, J. Tetrahedron Lett. 1995, 36, 4893-6. (b) Carren∼o, M. C.; Pérez González, M.; Houk, K. N. J. Org. Chem. 1997, 62, 9128-37.
18. Swiss, K. A.; Liotta, D. C.; Maryanoff, C. A J. Am. Chem. Soc. 1990, 112, 9393-4.
19. (a) Solomon, M.; Jamison, W. C. L.; McCormick, M.; Liotta, D. C.; Cherry, D. A.; Mills, J. E.; Shah, R. D.; Rodgers, J. D.; Maryanoff, C. A. J. Am. Chem. Soc. 1988, 110, 3702-4.
20. (b) Swiss, K. A; Hinkley, W.; Maryanoff, C. A.; Liotta, D. C. Synthesis 1992, 127-31.
21. Captain, L. F.; Xia, X.; Liotta, D. C. Tetrahedron Lett. 1996, 37, 4293-6.
22. Fujioka, H.; Kitagaki, S.; Ohno, N.; Kitagawa, H.; Kita, Y.; Matsumoto, K. Tetrahedron; Asymmetry 1994, 5, 333-6.
23. Lipshutz, B. H. In Organometallics in Synthesis: A Manual; Schlosser, M., Ed.; John Wiley & Sons: Chichester, 1994.
24. Aluminum derivatives had been successfully used in asymmetric additions to β-keto sulfoxides: (a) Bueno, A. B.; Carren∼o, M. C.; Garcia Ruano, J. L.; Pen∼a, B.; Rubio, A.; Hoyos, M. A. Tetrahedron 1994, 50, 9355-64. (h) Carren∼o, M. C.; García Ruano, J. L.; Maestro, M. C.; Pérez González, M. Tetrahedron 1993, 49, 11009-18. (c) Bueno, A. B.; Carren∼o, M. C.; García Ruano, J. L. Tetrahedron Lett. 1995, 36, 3737-40. (d) Escribano, A. M.; Garcia Ruano, J. L.; Martin-Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567-78.
25. Aluminum derivatives had been successfully used in asymmetric additions to β-keto sulfoxides: (a) Bueno, A. B.; Carren∼o, M. C.; Garcia Ruano, J. L.; Pen∼a, B.; Rubio, A.; Hoyos, M. A. Tetrahedron 1994, 50, 9355-64. (h) Carren∼o, M. C.; García Ruano, J. L.; Maestro, M. C.; Pérez González, M. Tetrahedron 1993, 49, 11009-18. (c) Bueno, A. B.; Carren∼o, M. C.; García Ruano, J. L. Tetrahedron Lett. 1995, 36, 3737-40. (d) Escribano, A. M.; Garcia Ruano, J. L.; Martin-Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567-78.
26. Aluminum derivatives had been successfully used in asymmetric additions to β-keto sulfoxides: (a) Bueno, A. B.; Carren∼o, M. C.; Garcia Ruano, J. L.; Pen∼a, B.; Rubio, A.; Hoyos, M. A. Tetrahedron 1994, 50, 9355-64. (h) Carren∼o, M. C.; García Ruano, J. L.; Maestro, M. C.; Pérez González, M. Tetrahedron 1993, 49, 11009-18. (c) Bueno, A. B.; Carren∼o, M. C.; García Ruano, J. L. Tetrahedron Lett. 1995, 36, 3737-40. (d) Escribano, A. M.; Garcia Ruano, J. L.; Martin-Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567-78.
27. Aluminum derivatives had been successfully used in asymmetric additions to β-keto sulfoxides: (a) Bueno, A. B.; Carren∼o, M. C.; Garcia Ruano, J. L.; Pen∼a, B.; Rubio, A.; Hoyos, M. A. Tetrahedron 1994, 50, 9355-64. (h) Carren∼o, M. C.; García Ruano, J. L.; Maestro, M. C.; Pérez González, M. Tetrahedron 1993, 49, 11009-18. (c) Bueno, A. B.; Carren∼o, M. C.; García Ruano, J. L. Tetrahedron Lett. 1995, 36, 3737-40. (d) Escribano, A. M.; Garcia Ruano, J. L.; Martin-Castro, A. M.; Rodríguez, J. H. Tetrahedron 1994, 50, 7567-78.
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