Solid-supported combinatorial synthesis of structurally diverse β-lactams

Journal of the American Chemical Society

Volumn 118, Issue 1, 1996, Pages 253-254

  Ruhland, Beatrice ^a   Bhandari, Ashok ^a   Gordon, Eric M ^a   Gallop, Mark A ^a  

^a AFFYMAX RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030064961     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953322p     Document Type: Article

References (27)

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11. (a) Tetrahydrofurans, see: Beebe, X.; Schore, N. E.; Kurth, M. J. J. Am. Chem. Soc. 1992, 114, 10061-10062.
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15. For a review, see: Georg, G. I.; Ravikumar, V. T. in The Organic Chemistry of β-Lactains; Georg. G. I., Ed.; Verlag Chemie: New York, 1993; pp 295-368.
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18. Georg, G. I.; Wu, Z. Tetrahedron Lett. 1994, 35, 381-384.
19. Evidence for formation of a trans β-lactam product was obtained in only one instance: 1-[(S)-1-carboxy-2-methylpropyl]-3-phenoxy-4-(2-pyridyl)-azetidin-2-one was isolated as a pair of cis and trans isomers in a 2:1 ratio.
20. (a) Ojima, I.; Chen, H.-J. C. J Chem. Soc., Chem. Commun. 1987, 625-626.
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23. Slusarchyk, W. A., Dejneka, T.; Gordon, E. M.; Weaver, E. R.; Koster, W. H. Heterocycles 1984, 21, 191-209.
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26. Loss of the resonance for the imine proton (δ = 8.00, d) and the appearance of a pair of doublets (δ = 5.49 and 5.35) corresponding H-3 of the azetidinone ring in major and minor cis diastereomeric products, respectively, is diagnostic for this cycloaddition. Resonances for the vinylic proton in these isomers are also seen as a pair of doublets (δ = 5.63 and 6.22). Note that photolytic release from the support removes the asymmetric benzylic center of the linker from the β-lactams, which are thus liberated as racemates.
27. Wild, H. In The Organic Chemistry of β-Lactams, Georg, G. I., Ed.; Verlag Chemie: New York, 1993, pp 1-48.