Cyclic sulfamidates as vehicles for the synthesis of substituted lactams

Organic Letters

Volumn 6, Issue 25, 2004, Pages 4727-4730

  Bower, John F ^a   Švenda, Jakub ^a   Williams, Andrew J ^a   Charmant, Jonathan P H ^a   Lawrence, Ron M ^b   Szeto, Peter ^b   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; ACETIC ACID DERIVATIVE; LACTAM DERIVATIVE; MALONIC ACID; PIPERIDONE DERIVATIVE; SULFAMIDATE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; LACTAMIZATION; SUBSTITUTION REACTION; SYNTHESIS;

EID: 11444250543     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048036+     Document Type: Article

References (27)

1. For a recent and very comprehensive review, see: Meléndez, R. E.; Lubell, W. D. Tetrahedron 2003, 59, 2581-2616.
2. 2,2-amino acids via 1,2-cyclic sulfamidates, see: Avenoza, A.; Busto, J. H.; Corzana, F.; Jiménez-Osés, G.; Peregrina, J. M. Chem. Commun. 2004, 980-981.
3. Williams, A. J.; Chakthong, S.; Gray, D.; Lawrence, R. M.; Gallagher, T. Org. Lett. 2003, 5, 811-814.
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7. 1
8. (a) Wehn, P. M.; Lee, J. H.; Du Bois, J. Org. Lett. 2003, 5, 4823-4826.
9. (b) Espino, C. G.; Wehn, P. M.; Chow, J.; Du Bois, J. J. Am. Chem. Soc. 2001, 123, 6935-6936.
10. 3 1,3-Cyclic sulfamidate 2c was prepared using the method of Du Bois. Subsequent N-benzylation was carried out under Tewson's phase transfer conditions. See Supporting Information. A more conventional approach to 2c from the corresponding amino alcohol was examined, but oxidation of the intermediate 1,3-cyclic sulfamidite was inefficient. Substrates 2a, 2b, and 2e were prepared using enantiomerically pure starting materials and 2c and 2d were racemic.
11. The structure of 3b was determined by X-ray crystallographic analysis. Details are available in Supporting Information.
12. α-Phosphonolactams analogous to 6a have been prepared previously in a number of different ways and utilized in olefination processes. For recent representative examples, see: Gois, P. M. P.; Afonso, C. A. M. Eur. J. Org. Chem. 2003, 3798-3810. Gois, P. M. P.; Afonso, C. A. M. Tetrahedron Lett. 2003, 44, 6571-6573. Du, Y. M.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5709-5717.
13. α-Phosphonolactams analogous to 6a have been prepared previously in a number of different ways and utilized in olefination processes. For recent representative examples, see: Gois, P. M. P.; Afonso, C. A. M. Eur. J. Org. Chem. 2003, 3798-3810. Gois, P. M. P.; Afonso, C. A. M. Tetrahedron Lett. 2003, 44, 6571-6573. Du, Y. M.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5709-5717.
14. α-Phosphonolactams analogous to 6a have been prepared previously in a number of different ways and utilized in olefination processes. For recent representative examples, see: Gois, P. M. P.; Afonso, C. A. M. Eur. J. Org. Chem. 2003, 3798-3810. Gois, P. M. P.; Afonso, C. A. M. Tetrahedron Lett. 2003, 44, 6571-6573. Du, Y. M.; Wiemer, D. F. J. Org. Chem. 2002, 67, 5709-5717.
15. 6
16. In the case of 9b, a 5:2 ratio of C(3) diastereomers was observed, while single (presumably thermodynamically more stable) diastereomers were seen for the corresponding malonate and phosphonate adducts 3b and 6b, respectively.
17. Mori, K.; Tominaga, M.; Takigawa, T.; Matsui, M. Synthesis 1973, 790-791.
18. Högberg, T.; Ström, P.; Ebner, M.; Rämsby, S. J. Org. Chem. 1987, 52, 2033-2036. For an earlier application of cyanide-mediated lactamization, see ref 3.
19. Our observations are that the initial nucleophilic displacement reaction involving 2c occurs efficiently, but the subsequent lactamization leading to a six-membered ring is more demanding. In addition to NaCN/ MeOH, lactamization to give 9c was also achieved using either p-xylene at reflux (37%) or EtONa/EtOH at reflux (23%).
20. A trend is apparent here. Sulfamidate 2a gives lowered yields of 3,5-disubstituted lactams as the enolate becomes more basic: 9a (88%); 12 (73%); 13 (65%). It is also pertinent to mention that attempts to use simple alkyl enolates, e.g., sodium ethyl propanoate, have failed.
21. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234-6235. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Che, C. M. J. Org. Chem. 2004, 69, 3610-3619. Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. Nicolaou, K. C.; Huang, X. H.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Yu, X. Q.; Huang, J. S.; Zhou, X. G.; Che, C. M. Org. Lett. 2000, 2, 2233-2236.
22. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234-6235. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Che, C. M. J. Org. Chem. 2004, 69, 3610-3619. Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. Nicolaou, K. C.; Huang, X. H.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Yu, X. Q.; Huang, J. S.; Zhou, X. G.; Che, C. M. Org. Lett. 2000, 2, 2233-2236.
23. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234-6235. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Che, C. M. J. Org. Chem. 2004, 69, 3610-3619. Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. Nicolaou, K. C.; Huang, X. H.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Yu, X. Q.; Huang, J. S.; Zhou, X. G.; Che, C. M. Org. Lett. 2000, 2, 2233-2236.
24. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234-6235. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Che, C. M. J. Org. Chem. 2004, 69, 3610-3619. Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. Nicolaou, K. C.; Huang, X. H.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Yu, X. Q.; Huang, J. S.; Zhou, X. G.; Che, C. M. Org. Lett. 2000, 2, 2233-2236.
25. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234-6235. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Che, C. M. J. Org. Chem. 2004, 69, 3610-3619. Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. Nicolaou, K. C.; Huang, X. H.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Yu, X. Q.; Huang, J. S.; Zhou, X. G.; Che, C. M. Org. Lett. 2000, 2, 2233-2236.
26. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234-6235. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Che, C. M. J. Org. Chem. 2004, 69, 3610-3619. Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. Nicolaou, K. C.; Huang, X. H.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Yu, X. Q.; Huang, J. S.; Zhou, X. G.; Che, C. M. Org. Lett. 2000, 2, 2233-2236.
27. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234-6235. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Che, C. M. J. Org. Chem. 2004, 69, 3610-3619. Fruit, C.; Müller, P. Tetrahedron: Asymmetry 2004, 15, 1019-1026. Liang, J. L.; Yuan, S. X.; Huang, J. S.; Yu, W. Y.; Che, C. M. Angew. Chem., Int. Ed. 2002, 41, 3465-3468. Duran, F.; Leman, L.; Ghini, A.; Burton, G.; Dauban, P.; Dodd, R. H. Org. Lett. 2002, 4, 2481-2483. Nicolaou, K. C.; Huang, X. H.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834-838. Yu, X. Q.; Huang, J. S.; Zhou, X. G.; Che, C. M. Org. Lett. 2000, 2, 2233-2236.