Novel N1-C4 β-lactam bond breakage. Synthesis of enantiopure γ-alkoxy-γ-keto acid derivatives

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1765-1767

  Alcaide, Benito ^a   Almendros, Pedro ^b   Redondo, María C ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 (TRIMETHYLSILYL)THIAZOLE; AZETIDINONE DERIVATIVE; BETA LACTAM; OXOACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; DRUG SYNTHESIS; STEREOCHEMISTRY; TEMPERATURE;

EID: 2942629617     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049549j     Document Type: Article

References (23)

1. For selected reviews, see: (a) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (c) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
2. For selected reviews, see: (a) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (c) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
3. For selected reviews, see: (a) Alcaide, B.; Almendros, P. Chem. Soc. Rev. 2001, 30, 226. (b) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Oiarbide, M. Synlett 2001, 1813. (c) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755.
4. For a review on the selective bond cleavage of the β-lactam nucleus, see: Alcaide, B.; Almendros, P. Synlett 2002, 381.
5. For reviews, see: (a) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (b) Ojima, I. Adv. Asymmetric Synth. 1995, 1, 95. (c) Ojima, I. Acc. Chem. Res. 1995, 28, 383.
6. For reviews, see: (a) Ojima, I.; Delaloge, F. Chem. Soc. Rev. 1997, 26, 377. (b) Ojima, I. Adv. Asymmetric Synth. 1995, 1, 95. (c) Ojima, I. Acc. Chem. Res. 1995, 28, 383.
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8. In addition to Ojima's work, the only available reports on the N1-C4 bond cleavage are: (a) Cabell, L. A.; McMurray, J. S. Tetrahedron Lett. 2002, 43, 2491. (b) Alcaide, B.; Domínguez, G.; Martín-Domenech, A.; Plumet, J.; Monge, A.; Pérez-García, V. Heterocycles 1987, 26, 1461.
9. In addition to Ojima's work, the only available reports on the N1-C4 bond cleavage are: (a) Cabell, L. A.; McMurray, J. S. Tetrahedron Lett. 2002, 43, 2491. (b) Alcaide, B.; Domínguez, G.; Martín-Domenech, A.; Plumet, J.; Monge, A.; Pérez-García, V. Heterocycles 1987, 26, 1461.
10. See, for instance: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2004, 69, 826. (c) Alcaide, B.; Almendros, P.; Alonso, J. M. Chem. Eur. J. 2003, 9, 5793. (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. (e) Alcaide. B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem. Eur. J. 2003, 9, 3415.
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12. See, for instance: (a) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993. (b) Alcaide, B.; Almendros, P.; Aragoncillo, C.; Rodríguez-Acebes, R. J. Org. Chem. 2004, 69, 826. (c) Alcaide, B.; Almendros, P.; Alonso, J. M. Chem. Eur. J. 2003, 9, 5793. (d) Alcaide, B.; Almendros, P.; Aragoncillo, C. Org. Lett. 2003, 5, 3795. (e) Alcaide. B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Chem. Eur. J. 2003, 9, 3415.
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23. For (-)-4a, see: (a) Alcaide, B.; Aly, M.; Rodríguez, C.; Rodríguez-Vicente, A. J. Org. Chem. 2000, 65, 3453. For (+)-4a and (+)-4b, see: (b) Wagle, D. R.; Garai, C.; Chiang, J.; Monteleone, M. G.; Kurys, B. E.; Strohmeyer, T. W.; Hedge, V. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1988, 53, 4227.