A single-pot, mild conversion of β-lactones to β-lactams

Journal of Organic Chemistry

Volumn 64, Issue 20, 1999, Pages 7657-7660

  Yang, Hong Woon ^a   Romo, Daniel ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0345466514     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990826n     Document Type: Article

References (35)

1. For reviews, see: (a) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacks, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 621. (b) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
2. For reviews, see: (a) Southgate, R.; Branch, C.; Coulton, S.; Hunt, E. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products; Lukacks, G., Ed.; Springer: Berlin, 1993; Vol. 2, p 621. (b) Southgate, R. Contemp. Org. Synth. 1994, 1, 417.
3. Palomo, C.; Aizpurua, J. M.; Ganoba, I. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH: New York, 1997; p 279.
4. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
5. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
6. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
7. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
8. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
9. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
10. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248-7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
11. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
12. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
13. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
14. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.-L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
15. For a review describing transformations of β-lactones, see: (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441-449. For some recent transformations, see: (b) Mead, K. T.; Lu, J. Tetrahedron Lett. 1994, 35, 8947-8950. (c) Ratemi, E. S.; Vederas, J. C. Tetrahedron Lett. 1994, 35, 7605-7608. (d) Zemribo, R.; Champ, M. S.; Romo, D. Synlett 1996, 278-280. (e) Mead, K. T.; Zemribo, R. Synlett 1996, 1065-1066. (f) Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196- 9201. (g) Dollinger, L. M.; Howell, A. R. J. Org. Chem. 1996, 61, 7248- 7249. (h) Zhao, C.; Romo, D. Tetrahedron Lett. 1997, 38, 6537-6540. (i) White, D.; Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1997, 38, 2223-2226. (j) Fujisawa, T.; Ito, T.; Nishiura, S.; Shimuzu. M. Tetrahedron Lett. 1998, 39, 9735-9738. (k) Machrouhi, F.; Namy, J.- L. Tetrahedron 1998, 54, 11111-11122. (l) Crich, D.; Mo, X.-S. J. Am. Chem. Soc. 1998, 120, 8298-8304.
16. For a recent report describing the conversion of β-hydroxy acids to β-lactams, see: Jin, Y.; Kim, D. H. Synlett 1998, 1189-1190.
17. For reviews on the synthesis and transformations of β-lactams, see: (a) Backes, J. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E., Bayer, O., Eds.; Thieme: Stuttgart, 1991; B and E16B, p 31. (b) Georg, G. I. The Organic Chemistry of β-Lactams; VCH Publishers: New York, 1993. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier Science Ltd.: Oxford, UK, 1996; Vol. 1B, pp 536-572.
18. For reviews on the synthesis and transformations of β-lactams, see: (a) Backes, J. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E., Bayer, O., Eds.; Thieme: Stuttgart, 1991; B and E16B, p 31. (b) Georg, G. I. The Organic Chemistry of β-Lactams; VCH Publishers: New York, 1993. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier Science Ltd.: Oxford, UK, 1996; Vol. 1B, pp 536-572.
19. For reviews on the synthesis and transformations of β-lactams, see: (a) Backes, J. In Houben-Weyl, Methoden der Organischen Chemie; Müller, E., Bayer, O., Eds.; Thieme: Stuttgart, 1991; B and E16B, p 31. (b) Georg, G. I. The Organic Chemistry of β-Lactams; VCH Publishers: New York, 1993. (c) De Kimpe, N. In Comprehensive Heterocyclic Chemistry II; Padwa, A., Ed.; Elsevier Science Ltd.: Oxford, UK, 1996; Vol. 1B, pp 536-572.
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25. 4-promoted reaction of aldehydes and silylketene acetals (β-lactone 1c: Wang, Y.; Zhao, C.; Romo, D., submitted), or by the [2 + 2] cycloaddition of silylketenes and aldehydes (β-lactone 1g; Yang, H. W.; Romo, D. Tetrahedron Lett. 1998, 39, 2877-2880).
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27. 4-promoted reaction of aldehydes and silylketene acetals (β-lactone 1c: Wang, Y.; Zhao, C.; Romo, D., submitted), or by the [2 + 2] cycloaddition of silylketenes and aldehydes (β-lactone 1g; Yang, H. W.; Romo, D. Tetrahedron Lett. 1998, 39, 2877-2880).
28. 4-promoted reaction of aldehydes and silylketene acetals (β-lactone 1c: Wang, Y.; Zhao, C.; Romo, D., submitted), or by the [2 + 2] cycloaddition of silylketenes and aldehydes (β-lactone 1g; Yang, H. W.; Romo, D. Tetrahedron Lett. 1998, 39, 2877-2880).
29. Coupling constants for trans-substituted β-lactams are typically in the range of J = 1.9-2.0 Hz while those for cis-substituted β-lactams are in the range of J = 5.3-5.5 Hz; see: Nelson, D. A. J. Org. Chem. 1972, 37, 1447-1448.
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