Synthesis and applications of C2-symmetric guanidine bases

Tetrahedron Letters

Volumn 44, Issue 48, 2003, Pages 8677-8680

  Allingham, Matthew T ^a   Howard Jones, Andrew ^a   Murphy, Patrick J ^a   Thomas, Dafydd A ^a   Caulkett, Peter W R ^b  

^a BANGOR UNIVERSITY   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

Catalysis; Guanidine; Phase transfer

Indexed keywords

GUANIDINE DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOSELECTIVITY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0142184536     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.09.162     Document Type: Article

References (27)

1. Caulkett P., Howard-Jones A., Murphy P.J., Thomas D. J. Org. Chem. 64:1999;1039-1041.
2. Saito S., Hasegawa T., Inaba M., Nishida R., Fujii T., Nomizu S., Moriwake T. Chem. Lett. 1984;1389-1392.
3. Alcazar V., Moran J.R., de Mendoza J. Tetrahedron Lett. 36:1995;3941-3944.
4. Nagasawa K., Georgieva A., Takahashi H., Nakata T. Tetrahedron. 57:2001;8959-8964.
5. Chinchilla R., Najera C., Sanchez-Agullo P. Tetrahedron: Asymmetry. 5:1994;1393-1402.
6. Ma D., Cheng K. Tetrahedron: Asymmetry. 10:1999;713-719.
7. Ishikawa T., Araki Y., Kumamoto T., Seki H., Fukuda K., Isobe T. Chem. Commun. 2001;245-246.
8. Trost B.M., Yeh V.S.C. Angew. Chem., Int. Ed. 41:2002;861-863.
9. Bakó P., Bajor Z., Tike L. J. Chem. Soc., Perkin Trans. 1. 1999;3651-3655.
10. For specific reviews, see: (a) Phase-Transfer Catalysis: Mechanisms and Syntheses; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997; (b) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; pp. 725-755; (c) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (d) T. Shioiri. In Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Chapman & Hall; London, 1997; pp. 462-479.
11. For specific reviews, see: (a) Phase-Transfer Catalysis: Mechanisms and Syntheses; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997; (b) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; pp. 725-755; (c) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (d) T. Shioiri. In Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Chapman & Hall; London, 1997; pp. 462-479.
12. For specific reviews, see: (a) Phase-Transfer Catalysis: Mechanisms and Syntheses; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997; (b) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; pp. 725-755; (c) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (d) T. Shioiri. In Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Chapman & Hall; London, 1997; pp. 462-479.
13. For specific reviews, see: (a) Phase-Transfer Catalysis: Mechanisms and Syntheses; Halpern, M. E., Ed.; American Chemical Society: Washington, DC, 1997; (b) O'Donnell, M. J. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; VCH: New York, 2000; pp. 725-755; (c) Nelson, A. Angew. Chem., Int. Ed. 1999, 38, 1583-1585; (d) T. Shioiri. In Handbook of Phase Transfer Catalysis; Sasson, Y.; Neumann, R., Eds.; Chapman & Hall; London, 1997; pp. 462-479.
14. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
15. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
16. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
17. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
18. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
19. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
20. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
21. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
22. For this reaction and other related PTC alkylations, see: (a) O'Donnell, M. J.; Wu, S.; Hoffman, C. Tetrahedron 1994, 50, 4507-4518; (b) Lygo, B.; Wainwright, P. G. Tetrahedron Lett. 1997, 38, 8595-8598; (c) Lygo, B.; Crosby, J.; Peterson, J. A. Tetrahedron Lett. 1999, 40, 1385-1388; (d) Lygo, B. Tetrahedron Lett. 1999, 40, 1389-1392; (e) Lygo, B.; Crosby, J.; Lowdon, T. R.; Peterson, J. A.; Wainwright, P. G. Tetrahedron 2001, 57, 2403-2409; (f) Corey, E. J.; Xu, F.; Noe, M. C. J. Am. Chem. Soc. 1997, 119, 12414-12415; (g) Corey, E. J.; Noe, M. C.; Xu, F. Tetrahedron Lett. 1998, 39, 5347-5350; (h) Corey, E. J.; Bo, Y.; Busch-Petersen, J. J. Am. Chem. Soc. 1998, 120, 13000-13001; (i) Ooi, T.; Kameda, M.; Maruoka, K. J. Am. Chem. Soc. 1999, 121, 6519-6520.
23. 1H NMR and ees (±3%) were determined on a Bakerbond DNPG column (98.5:1.5 hexane:dioxane).
24. Kita T., Georgieva A., Hashimoto Y., Nakata T., Nagasawa K. Angew. Chem., Int. Ed. 41:2002;2032-2034.
25. Lygo B., Wainwright P.G. Tetrahedron Lett. 39:1998;1599-1602.
26. Lygo B., Wainwright P.G. Tetrahedron. 55:1999;6289-6300.
27. 13).