Inverted diastereoselectivity in asymmetric aziridine synthesis via aza-Darzens reaction of (2S)-N-bromoacyl camphorsultam

Organic Letters

Volumn 1, Issue 9, 1999, Pages 1339-1341

  McLaren, Andrew B ^a   Sweeney, J B ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000473506     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990874u     Document Type: Article

References (16)

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2. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249. Sodergren, M. J.; Alonso, D. A.; Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897. Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. Sodergren, M. J.; Alonso, D. A.; Andersson, P. G. Tetrahedron: Asymmetry 1997, 8, 3563.
3. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249. Sodergren, M. J.; Alonso, D. A.; Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897. Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. Sodergren, M. J.; Alonso, D. A.; Andersson, P. G. Tetrahedron: Asymmetry 1997, 8, 3563.
4. Davis, F. A.; McCoull, W. Tetrahedron Lett. 1999, 40, 249. Sodergren, M. J.; Alonso, D. A.; Bedekar, A. V.; Andersson, P. G. Tetrahedron Lett. 1997, 38, 6897. Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693. Sodergren, M. J.; Alonso, D. A.; Andersson, P. G. Tetrahedron: Asymmetry 1997, 8, 3563.
5. Cantrill, A. A.; Hall, L. D.; Jarvis, A. N.; Osborn, H. M. I.; Raphy, J.; Sweeney, J. B. J. Chem. Soc., Chem. Commun. 1996, 2631.
6. +, 594.1508).
7. Asymmetric aza-Darzens and Darzens-like reactions: Gennari, C.; Pain, G. Tetrahedron Lett. 1996, 37, 3747. Fujisawa, T.; Hayakawa, R.; Shimizu M. Tetrahedron Lett. 1992, 33, 7903. Davis, F. A.; Zhou P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243. Davis, F. A.; Zhou, P.; Liang, C. H.; Reddy, R. E. Tetrahedron: Asymmetry 1995, 6, 1511. Florio, S.; Troisi L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
8. Asymmetric aza-Darzens and Darzens-like reactions: Gennari, C.; Pain, G. Tetrahedron Lett. 1996, 37, 3747. Fujisawa, T.; Hayakawa, R.; Shimizu M. Tetrahedron Lett. 1992, 33, 7903. Davis, F. A.; Zhou P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243. Davis, F. A.; Zhou, P.; Liang, C. H.; Reddy, R. E. Tetrahedron: Asymmetry 1995, 6, 1511. Florio, S.; Troisi L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
9. Asymmetric aza-Darzens and Darzens-like reactions: Gennari, C.; Pain, G. Tetrahedron Lett. 1996, 37, 3747. Fujisawa, T.; Hayakawa, R.; Shimizu M. Tetrahedron Lett. 1992, 33, 7903. Davis, F. A.; Zhou P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243. Davis, F. A.; Zhou, P.; Liang, C. H.; Reddy, R. E. Tetrahedron: Asymmetry 1995, 6, 1511. Florio, S.; Troisi L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
10. Asymmetric aza-Darzens and Darzens-like reactions: Gennari, C.; Pain, G. Tetrahedron Lett. 1996, 37, 3747. Fujisawa, T.; Hayakawa, R.; Shimizu M. Tetrahedron Lett. 1992, 33, 7903. Davis, F. A.; Zhou P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243. Davis, F. A.; Zhou, P.; Liang, C. H.; Reddy, R. E. Tetrahedron: Asymmetry 1995, 6, 1511. Florio, S.; Troisi L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
11. Asymmetric aza-Darzens and Darzens-like reactions: Gennari, C.; Pain, G. Tetrahedron Lett. 1996, 37, 3747. Fujisawa, T.; Hayakawa, R.; Shimizu M. Tetrahedron Lett. 1992, 33, 7903. Davis, F. A.; Zhou P.; Reddy, G. V. J. Org. Chem. 1994, 59, 3243. Davis, F. A.; Zhou, P.; Liang, C. H.; Reddy, R. E. Tetrahedron: Asymmetry 1995, 6, 1511. Florio, S.; Troisi L.; Capriati, V. J. Org. Chem. 1995, 60, 2279.
12. Zimmerman, H. E. J. Am. Chem. Soc. 1957, 79, 1920.
13. Calculations (UFF, Rapper, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024) show the Z-enolate to be more stable than the E-enolate by 4.1 kcal/mol.
14. P-H = 32 Hz) in the pure state, (E)-(Z)-isomerism of imines under the influence of metal ions is well-known; see, for example: Alshalaan, A. M.; Alshowiman, S. S.; Alnajjar, I. M. Inorg. Chim. Acta 1986, 121, 127-129. For a discussion of the factors underlying (E)/(Z)-preferences in imines, see: Bjørgo, J.; Boyd, D. R.; Watson, C. G.; Jennings, W. B. J. Chem. Soc., Perkin Trans. I 1974, 757.
15. P-H = 32 Hz) in the pure state, (E)-(Z)-isomerism of imines under the influence of metal ions is well-known; see, for example: Alshalaan, A. M.; Alshowiman, S. S.; Alnajjar, I. M. Inorg. Chim. Acta 1986, 121, 127-129. For a discussion of the factors underlying (E)/(Z)-preferences in imines, see: Bjørgo, J.; Boyd, D. R.; Watson, C. G.; Jennings, W. B. J. Chem. Soc., Perkin Trans. I 1974, 757.
16. Streitwieser, A.; Heathcock, C. H.; Kosower, E. M. Introduction to Organic Chemistry; Macmillian Publishing Company: New York, 1992.