Catalytic asymmetric staudinger reactions to form β-lactams: An unanticipated dependence of diastereoselectivity on the choice of the nitrogen substituent

Journal of the American Chemical Society

Volumn 127, Issue 33, 2005, Pages 11586-11587

  Lee, Elaine C ^a   Hodous, Brian L ^a   Bergin, Enda ^a   Shih, Crystal ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM; NITROGEN;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL ANALYSIS; DIASTEREOISOMER; ENANTIOSELECTIVITY; EPIMERIZATION; REACTION ANALYSIS; STAUDINGER REACTION; STEREOCHEMISTRY;

BETA-LACTAMS; CATALYSIS; MOLECULAR STRUCTURE; NITROGEN; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 24044436551     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052058p     Document Type: Article

References (31)

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2. (b) Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: New York, 1996; Chapters 1.18-1.20.
3. (c) Chemistry and Biology of Beta-Lactam Antibiotics; Morin, R. B., Gorman, M., Eds.; Academic: New York, 1982; Vols. 1-3.
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8. Staudinger, H. Liebigs Ann. Chem. 1907, 356, 51-123.
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12. For leading references to uncommon trans-selective processes, see: (a) Liang, Y.; Jiao, E.; Zhang, S.; Xu, J. J. Org. Chem. 2005, 70, 334-337.
13. (b) ref 4b.
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17. (b) In addition, Lectka has described a catalytic asymmetric Staudinger reaction of a symmetrical disubstituted ketene (for which there is no issue of diastereoselectivity): Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. J. Am. Chem. Soc. 2000, 122, 7831-7832.
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19. (b) France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. J. Am. Chem. Soc. 2005, 127, 1206-1215 and references therein.
20. We use the terms cis and trans as a shorthand means of describing the position of the C3 aryl group relative to the C4 substituent.
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25. 2 and/or toluene).
26. (b) Under identical conditions, but in the absence of catalyst, no β-lactam is produced.
27. (c) If desired, the catalyst can generally be recovered in >70% yield.
28. Firestone, R. A.; Barker, P. L.; Pisano, J. M.; Ashe, B. M.; Dahlgren, M. E. Tetrahedron 1990, 46, 2255-2262.
29. For the use of this reagent to remove a Ts group from a sulfonamide, see: Nayak, S. K. Synthesis 2000, 1575-1578.
30. For an X-ray crystal structure of A, see the Supporting Information.
31. 1H NMR study, we believe that the resting state of the catalyst during Staudinger reactions of N-triflyl imines may be adduct B (Figure 2). (2) An initial kinetics investigation indicates that (a) the rate law is first-order in catalyst and zero-order in ketene and imine; (b) there is a substantial normal α secondary kinetic isotope effect for reactions of undeuterated versus monodeuterated imines.