Asymmetric aziridine synthesis via aza-Darzens reaction of bromoacylcamphorsultam

Chemical Communications

Volumn , Issue 23, 1996, Pages 2631-2632

  Cantrill, Alex A ^a   Hall, Lee D ^a   Jarvis, Ashley N ^a   Osborn, Helen M I ^a   Raphy, Jenny ^b   Sweeney, J B ^a,c  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^c UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001932039     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960002631     Document Type: Article

References (30)

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4. R. S. Atkinson, M. P. Coogan and I. S. T. Lochrie, Chem. Commun., 1996, 789; R. S. Atkinson and P. J. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 205; R. S. Atkinson, M. P. Coogan and D. Cornell, J. Chem. Soc., Perkin Trans. 1, 1996, 1572; K. G. Rasmussen and K. A. Jorgensen, J. Chem. Soc., Chem. Commun., 1995, 1401; M. Moran, G. Bernardinelli and P. Muller, Helv. Chim. Acta, 1995, 78, 2048; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326.
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6. R. S. Atkinson, M. P. Coogan and I. S. T. Lochrie, Chem. Commun., 1996, 789; R. S. Atkinson and P. J. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 205; R. S. Atkinson, M. P. Coogan and D. Cornell, J. Chem. Soc., Perkin Trans. 1, 1996, 1572; K. G. Rasmussen and K. A. Jorgensen, J. Chem. Soc., Chem. Commun., 1995, 1401; M. Moran, G. Bernardinelli and P. Muller, Helv. Chim. Acta, 1995, 78, 2048; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326.
7. R. S. Atkinson, M. P. Coogan and I. S. T. Lochrie, Chem. Commun., 1996, 789; R. S. Atkinson and P. J. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 205; R. S. Atkinson, M. P. Coogan and D. Cornell, J. Chem. Soc., Perkin Trans. 1, 1996, 1572; K. G. Rasmussen and K. A. Jorgensen, J. Chem. Soc., Chem. Commun., 1995, 1401; M. Moran, G. Bernardinelli and P. Muller, Helv. Chim. Acta, 1995, 78, 2048; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326.
8. R. S. Atkinson, M. P. Coogan and I. S. T. Lochrie, Chem. Commun., 1996, 789; R. S. Atkinson and P. J. Williams, J. Chem. Soc., Perkin Trans. 2, 1996, 205; R. S. Atkinson, M. P. Coogan and D. Cornell, J. Chem. Soc., Perkin Trans. 1, 1996, 1572; K. G. Rasmussen and K. A. Jorgensen, J. Chem. Soc., Chem. Commun., 1995, 1401; M. Moran, G. Bernardinelli and P. Muller, Helv. Chim. Acta, 1995, 78, 2048; D. A. Evans, M. M. Faul and M. T. Bilodeau, J. Am. Chem. Soc., 1994, 116, 2742; Z. Li, K. R. Conser and E. N. Jacobsen, J. Am. Chem. Soc., 1993, 115, 5326.
9. A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; A. A. Cantrill and J. B. Sweeney, Synlett, 1995, 1277; A. A. Cantrill, H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 3159; H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 2739; H. M. I. Osborn, J. B. Sweeney and W. Howson, Synlett, 1994, 145. N-Phosphorylated aziridines have also been reported to undergo efficient ring-opening reactions: A. Zwierzak and A. Napieraj, Tetrahedron. 1996, 52, 8789; K. Osowskapacewicka and A. Zwierzak, Pol. J. Chem., 1994, 68, 1263.
10. A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; A. A. Cantrill and J. B. Sweeney, Synlett, 1995, 1277; A. A. Cantrill, H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 3159; H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 2739; H. M. I. Osborn, J. B. Sweeney and W. Howson, Synlett, 1994, 145. N-Phosphorylated aziridines have also been reported to undergo efficient ring-opening reactions: A. Zwierzak and A. Napieraj, Tetrahedron. 1996, 52, 8789; K. Osowskapacewicka and A. Zwierzak, Pol. J. Chem., 1994, 68, 1263.
11. A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; A. A. Cantrill and J. B. Sweeney, Synlett, 1995, 1277; A. A. Cantrill, H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 3159; H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 2739; H. M. I. Osborn, J. B. Sweeney and W. Howson, Synlett, 1994, 145. N-Phosphorylated aziridines have also been reported to undergo efficient ring-opening reactions: A. Zwierzak and A. Napieraj, Tetrahedron. 1996, 52, 8789; K. Osowskapacewicka and A. Zwierzak, Pol. J. Chem., 1994, 68, 1263.
12. A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; A. A. Cantrill and J. B. Sweeney, Synlett, 1995, 1277; A. A. Cantrill, H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 3159; H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 2739; H. M. I. Osborn, J. B. Sweeney and W. Howson, Synlett, 1994, 145. N-Phosphorylated aziridines have also been reported to undergo efficient ring-opening reactions: A. Zwierzak and A. Napieraj, Tetrahedron. 1996, 52, 8789; K. Osowskapacewicka and A. Zwierzak, Pol. J. Chem., 1994, 68, 1263.
13. A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; A. A. Cantrill and J. B. Sweeney, Synlett, 1995, 1277; A. A. Cantrill, H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 3159; H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 2739; H. M. I. Osborn, J. B. Sweeney and W. Howson, Synlett, 1994, 145. N-Phosphorylated aziridines have also been reported to undergo efficient ring-opening reactions: A. Zwierzak and A. Napieraj, Tetrahedron. 1996, 52, 8789; K. Osowskapacewicka and A. Zwierzak, Pol. J. Chem., 1994, 68, 1263.
14. A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; A. A. Cantrill and J. B. Sweeney, Synlett, 1995, 1277; A. A. Cantrill, H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 3159; H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 2739; H. M. I. Osborn, J. B. Sweeney and W. Howson, Synlett, 1994, 145. N-Phosphorylated aziridines have also been reported to undergo efficient ring-opening reactions: A. Zwierzak and A. Napieraj, Tetrahedron. 1996, 52, 8789; K. Osowskapacewicka and A. Zwierzak, Pol. J. Chem., 1994, 68, 1263.
15. A. A. Cantrill, A. N. Jarvis, H. M. I. Osborn, A. Ouadi and J. B. Sweeney, Synlett, 1996, 847; A. A. Cantrill and J. B. Sweeney, Synlett, 1995, 1277; A. A. Cantrill, H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 3159; H. M. I. Osborn, J. B. Sweeney and W. Howson, Tetrahedron Lett., 1994, 35, 2739; H. M. I. Osborn, J. B. Sweeney and W. Howson, Synlett, 1994, 145. N-Phosphorylated aziridines have also been reported to undergo efficient ring-opening reactions: A. Zwierzak and A. Napieraj, Tetrahedron. 1996, 52, 8789; K. Osowskapacewicka and A. Zwierzak, Pol. J. Chem., 1994, 68, 1263.
16. N. J. Church and D. W. Young, Tetrahedron Lett., 1995, 36, 151.
17. Asymmetric aza-Darzens and Darzens-like reactions: C. Gennari and G. Pain, Tetrahedron Lett., 1996, 37, 3747; T. Fujisawa, R. Hayakawa and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; S. Florio, L. Troisi and V. Capriati, J. Org. Chem., 1995, 60, 2279. For Examples of diastereoselective Gabriel-Cromwell reaction, see: G. Cardillo, I. Gentilucci, C. Tomasini and M. P. V. Castejonbordas, Tetrahedron: Asymmetry, 1996, 7, 755; P. Garner, O. Dogan and S. Pillai, Tetrahedron Lett., 1994, 35, 1653.
18. Asymmetric aza-Darzens and Darzens-like reactions: C. Gennari and G. Pain, Tetrahedron Lett., 1996, 37, 3747; T. Fujisawa, R. Hayakawa and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; S. Florio, L. Troisi and V. Capriati, J. Org. Chem., 1995, 60, 2279. For Examples of diastereoselective Gabriel-Cromwell reaction, see: G. Cardillo, I. Gentilucci, C. Tomasini and M. P. V. Castejonbordas, Tetrahedron: Asymmetry, 1996, 7, 755; P. Garner, O. Dogan and S. Pillai, Tetrahedron Lett., 1994, 35, 1653.
19. Asymmetric aza-Darzens and Darzens-like reactions: C. Gennari and G. Pain, Tetrahedron Lett., 1996, 37, 3747; T. Fujisawa, R. Hayakawa and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; S. Florio, L. Troisi and V. Capriati, J. Org. Chem., 1995, 60, 2279. For Examples of diastereoselective Gabriel-Cromwell reaction, see: G. Cardillo, I. Gentilucci, C. Tomasini and M. P. V. Castejonbordas, Tetrahedron: Asymmetry, 1996, 7, 755; P. Garner, O. Dogan and S. Pillai, Tetrahedron Lett., 1994, 35, 1653.
20. Asymmetric aza-Darzens and Darzens-like reactions: C. Gennari and G. Pain, Tetrahedron Lett., 1996, 37, 3747; T. Fujisawa, R. Hayakawa and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; S. Florio, L. Troisi and V. Capriati, J. Org. Chem., 1995, 60, 2279. For Examples of diastereoselective Gabriel-Cromwell reaction, see: G. Cardillo, I. Gentilucci, C. Tomasini and M. P. V. Castejonbordas, Tetrahedron: Asymmetry, 1996, 7, 755; P. Garner, O. Dogan and S. Pillai, Tetrahedron Lett., 1994, 35, 1653.
21. Asymmetric aza-Darzens and Darzens-like reactions: C. Gennari and G. Pain, Tetrahedron Lett., 1996, 37, 3747; T. Fujisawa, R. Hayakawa and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; S. Florio, L. Troisi and V. Capriati, J. Org. Chem., 1995, 60, 2279. For Examples of diastereoselective Gabriel-Cromwell reaction, see: G. Cardillo, I. Gentilucci, C. Tomasini and M. P. V. Castejonbordas, Tetrahedron: Asymmetry, 1996, 7, 755; P. Garner, O. Dogan and S. Pillai, Tetrahedron Lett., 1994, 35, 1653.
22. Asymmetric aza-Darzens and Darzens-like reactions: C. Gennari and G. Pain, Tetrahedron Lett., 1996, 37, 3747; T. Fujisawa, R. Hayakawa and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; S. Florio, L. Troisi and V. Capriati, J. Org. Chem., 1995, 60, 2279. For Examples of diastereoselective Gabriel-Cromwell reaction, see: G. Cardillo, I. Gentilucci, C. Tomasini and M. P. V. Castejonbordas, Tetrahedron: Asymmetry, 1996, 7, 755; P. Garner, O. Dogan and S. Pillai, Tetrahedron Lett., 1994, 35, 1653.
23. Asymmetric aza-Darzens and Darzens-like reactions: C. Gennari and G. Pain, Tetrahedron Lett., 1996, 37, 3747; T. Fujisawa, R. Hayakawa and M. Shimizu, Tetrahedron Lett., 1992, 33, 7903; F. A. Davis, P. Zhou and G. V. Reddy, J. Org. Chem., 1994, 59, 3243; F. A. Davis, P. Zhou, C. H. Liang and R. E. Reddy, Tetrahedron: Asymmetry, 1995, 6, 1511; S. Florio, L. Troisi and V. Capriati, J. Org. Chem., 1995, 60, 2279. For Examples of diastereoselective Gabriel-Cromwell reaction, see: G. Cardillo, I. Gentilucci, C. Tomasini and M. P. V. Castejonbordas, Tetrahedron: Asymmetry, 1996, 7, 755; P. Garner, O. Dogan and S. Pillai, Tetrahedron Lett., 1994, 35, 1653.
24. For pertinent leading references as to the synthetic utility of the camphorsulfonyl group as a chiral auxiliary, see A. C. Spivey, Encyclopaedia of Reagents for Organic Synthesis, 1995, vol. 2, p. 975.
25. All N-diphenylphosphinyl imines were prepared according to: W. B. Jennings and C. J. Lovely, Tetrahedron, 1991, 47, 5561.
26. K. B. Hansen, N. S. Finney and E. N. Jacobsen, Angew. Chem., Int. Ed. Engl., 1995, 34, 676.
27. Asymmetric Darzens reaction: A. F. Abdelmagid, L. N. Pridgen, D. S. Eggleston and I. Lantos, J. Am. Chem. Soc., 1986, 108, 4595; E. J. Corey and S. Choi, Tetrahedron Lett., 1991, 32, 2857; L. N. Pridgen, A. F. Abdelmagid, I. Lantos, S. Shilcrat and D. S. Eggleston, J. Org. Chem., 1993, 58, 5107.
28. Asymmetric Darzens reaction: A. F. Abdelmagid, L. N. Pridgen, D. S. Eggleston and I. Lantos, J. Am. Chem. Soc., 1986, 108, 4595; E. J. Corey and S. Choi, Tetrahedron Lett., 1991, 32, 2857; L. N. Pridgen, A. F. Abdelmagid, I. Lantos, S. Shilcrat and D. S. Eggleston, J. Org. Chem., 1993, 58, 5107.
29. Asymmetric Darzens reaction: A. F. Abdelmagid, L. N. Pridgen, D. S. Eggleston and I. Lantos, J. Am. Chem. Soc., 1986, 108, 4595; E. J. Corey and S. Choi, Tetrahedron Lett., 1991, 32, 2857; L. N. Pridgen, A. F. Abdelmagid, I. Lantos, S. Shilcrat and D. S. Eggleston, J. Org. Chem., 1993, 58, 5107.
30. Siemens Analytical X-Ray, Ltd., Madison, Wisconsin, USA.