β-lactam synthesis by the Kinugasa reaction

Angewandte Chemie - International Edition

Volumn 43, Issue 17, 2004, Pages 2198-2200

  Marco Contelles, José ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

lactams; Kinugasa reaction; Nitrones; Synthetic methods

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBONS;

HETEROCYCLES; KINUGASA REACTIONS; LACTUM SYNTHESIS;

SYNTHESIS (CHEMICAL);

BETA LACTAM DERIVATIVE; HETEROCYCLIC COMPOUND;

ASYMMETRIC SYNTHESIS; CHEMICAL REACTION; DRUG ACTIVITY; DRUG SYNTHESIS; METHODOLOGY; SHORT SURVEY;

EID: 3042527462     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200301730     Document Type: Short Survey

References (22)

1. a) Comprehensive Heterocyclic Chemistry II (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, New York, 1996, chap. 1.18-1.20;
2. b) I. Ojima, F. Delaloge, Chem. Soc. Rev. 1997, 26, 377-386;
3. c) I. Ojima, Acc. Chem. Res. 1995, 28, 383-389;
4. d) P.A. Magriotis, Angew. Chem. 2001, 113, 4507-4509; Angew. Chem. Int. Ed. 2001, 40, 4377-4379.
5. d) P.A. Magriotis, Angew. Chem. 2001, 113, 4507-4509; Angew. Chem. Int. Ed. 2001, 40, 4377-4379.
6. Synthesis of β-Lactam Antibiotics Chemistry, Biocatalysis and Process Integration (Ed.: A. Bruggink), Kluwer, Dordrecht, Netherlands, 2001.
7. M. Kinugasa, S. Hashimoto, J. Chem. Soc. Chem. Commun. 1972, 466-467.
8. a) R. Huisgen, H. Seidl, Tetrahedron Lett. 1963, 2019-2022.
9. The reaction of silylacetylenes with aldonitrones affords monocyclic β-lactams after treatment of the intermediate 5-(trimethylsilyl) isoxazolines with base: b) C. Ahn, J. W. Kennington, P. DeShong, J. Org. Chem. 1994, 59, 6282-6286.
10. L. K. Ding, W. J. Irwin, J. Chem. Soc. Perkin Trans. 1 1976, 2382-2386.
11. a) D. K. Dutta, R. C. Boruah, J. S. Sandhu, Heterocycles 1986, 24, 655-658;
12. b) D. K. Dutta, R. C. Boruah, J. S. Sandhu, Indian J. Chem. Sect. B 1986, 25, 350-353.
13. a) K. Okuro, M. Enna, M. Miura, M. Nomura, J. Chem. Soc. Chem. Commun. 1993, 1107-1108;
14. b) M. Miura, M. Enna, K. Okuro, M. Nomura, J. Org. Chem. 1995, 60, 4999-5004.
15. a) A. Basak, T. Mahato, G. Bhattacharya, B. Mukherjee, Tetrahedron Lett. 1997, 38, 643-646;
16. b) A. Basak, G. Bhattacharya, H. M. M. Bdour, Tetrahedron 1998, 54, 6529-6538.
17. A. Basak, S. C. Ghosh, T. Bhowmick, A. K. Das, V. Bertolasi, Tetrahedron Lett. 2002, 43, 5499-5501.
18. M. M.-C. Lo, G. C. Fu, J. Am. Chem. Soc. 2002, 124, 4572-4573.
19. M.-C. Ye, J. Zhou, Z.-Z. Huang, Y. Tang, Chem. Commun. 2003, 2554-2555.
20. R. Shintani, G. C. Fu, Angew. Chem. 2003, 115, 4216-4219; Angew. Chem. Int. Ed. 2003, 42, 4082-4085.
21. R. Shintani, G. C. Fu, Angew. Chem. 2003, 115, 4216-4219; Angew. Chem. Int. Ed. 2003, 42, 4082-4085.
22. R. Shintani, G. C. Fu, Org. Lett. 2002, 4, 3699-3702.