Diastereoselective Baylis-Hillman reaction of 4-oxoazetidine-2-carbaldehydes: Rapid, stereocontrolled and divergent radical synthesis of highly functionalised β-lactams fused to medium rings

Chemical Communications

Volumn , Issue 18, 1999, Pages 1913-1914

  Alcaide, Benito ^a   Almendros, Pedro ^a   Aragoncillo, Cristina ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; RADICAL;

ARTICLE; CHEMICAL STRUCTURE; DIASTEREOISOMER;

EID: 0033592445     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905017e     Document Type: Article

References (19)

1. Reviews: E. Ciganek, Org. React., 1997, 51, 201; D. Basavaiah, P. D. Rao and R. S. Hyma, Tetrahedron, 1996, 52, 8001.
2. Reviews: E. Ciganek, Org. React., 1997, 51, 201; D. Basavaiah, P. D. Rao and R. S. Hyma, Tetrahedron, 1996, 52, 8001.
3. For leading references, see: D. P. Curran, N. A. Porter and B. Giese, in Stereochemistry of Radical Reactions, VCH Publishers, New York, 1996; D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1992, vol 4, ch. 4.2.
4. For leading references, see: D. P. Curran, N. A. Porter and B. Giese, in Stereochemistry of Radical Reactions, VCH Publishers, New York, 1996; D. P. Curran, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1992, vol 4, ch. 4.2.
5. See, for example: D. Niccolai, L. Tarsi and R. J. Thomas, Chem. Commun., 1997, 2333; V. Hook, Chem. Br., 1997, 33, 34 ; J. Davies, Science, 1994, 264, 375.
6. See, for example: D. Niccolai, L. Tarsi and R. J. Thomas, Chem. Commun., 1997, 2333; V. Hook, Chem. Br., 1997, 33, 34 ; J. Davies, Science, 1994, 264, 375.
7. See, for example: D. Niccolai, L. Tarsi and R. J. Thomas, Chem. Commun., 1997, 2333; V. Hook, Chem. Br., 1997, 33, 34 ; J. Davies, Science, 1994, 264, 375.
8. See for example: Symposia-in-Print Number 8, Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactam antibiotics, ed. G. I. Georg, Bioorg. Med. Chem. Lett., 1993, 3, 2159.
9. B. Alcaide and P. Almendros, Tetrahedron Lett., 1999, 40, 1015.
10. J. Knight, P. J. Parsons and R. Southgate, J. Chem. Soc., Chem. Commun. 1986, 78; J. Knight and P. J. Parsons, J. Chem. Soc., Perkin Trans. 1 1987, 1237.
11. J. Knight, P. J. Parsons and R. Southgate, J. Chem. Soc., Chem. Commun. 1986, 78; J. Knight and P. J. Parsons, J. Chem. Soc., Perkin Trans. 1 1987, 1237.
12. M. D. Bachi, F. Frolow and C. Hoornaert, J. Org. Chem., 1983, 48, 1841.
13. D. L. Boger and R. Mathvink, J. Org. Chem., 1988, 53, 3377.
14. G. I. Georg and V. T. Ravikumar, in The Organic Chemistry of β-Lactams, ed. G. I. Georg, VCH, Weinheim, 1993, ch. 3, p. 295.
15. S. E. Drewes, A. A. Khan and K. Rowland, Synth. Commun., 1993, 23, 183.
16. W. B. Motherwell and D. Crich, in Free Radical Chain Reactions in Organic Synthesis, Academic Press, London, 1991, ch. 6, pp. 183-185 and references cited therein.
17. B. Alcaide, I. M. Rodríguez-Campos, J. Rodríguez-Lopez and A. Rodríguez-Vincente, J. Org. Chem., 1999, 64, 5377.
18. The only related example is by Parsons et al. and refers to the cyclization of N-(2-bromoprop-2-en-1-yl)-4-allylazetidin-2-one to yield a homocarbacephem derivative. See ref. 6.
19. B. Giese, M. Bulliard, J. Dickhaut, R. Halbach, C. Hassler, U. Hoffmann, B. Hinzen and M. Senn, Synlett, 1995, 116.