The mechanism of the ketene-imine (Staudinger) reaction in its centennial: Still an unsolved problem?

Accounts of Chemical Research

Volumn 41, Issue 8, 2008, Pages 925-936

  Cossío, Fernando P ^a   Arrieta, Ana ^a   Sierra, Miguel A ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 51649103509     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800033j     Document Type: Article

References (56)

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44. Podlech et al also proposed a possible imine isomerization in the photochemically induced Staudinger reaction. See, for example: (a) Linder, M. R.; Frey, W. U.; Podlech, J. Diazoketenes as precursors in β-lactam synthesis. New insights into the mechanism of the photochemically induced Staudinger reaction. J. Chem. Soc., Perkin Trans. 1 2001, 256, 6-2577.
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49. (a) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Román, P.; Luque, A.; Martinez-Ripoll, M. Contribution to the development of new substitution patterns of optically active β-lactams: Synthesis of homochiral 4-(1-aminoalkyl)azetidin-2-ones fron N-(tert-butoxycarbonyl) α-amino aldehyde-derived imines via asymmetric Staudinger reaction. J. Am. Chem. Soc. 1992, 114, 9360-9369, and the pertinent references therein.
50. (b) Palomo, C.; Cossío, F. P.; Ontoria, J. M.; Odriozola, J. M. Preparation of chiral 3-unsubstituted β-lactams from 3-hydroxy-β- lactams by using the alkoxyketene-imine cycloaddition reaction as an approach to the azetidinone ring: A formal synthesis of the carbapenem antibiotic (+)-PS-5. Tetrahedron Lett. 1991, 32, 3105-3108.
51. Arrieta, A.; Cossio, F. P.; Lecea, B. New insights on the origins of the stereocontrol in the Staudinger reaction: [2 + 2] cycloaddition between ketenes and N-silylimines. J. Org. Chem. 2000, 65, 8458-8464.
52. Taggi, A. E.; Hafez, A. M.; Wack, H.; Young, B.; Drury, W. J., III; Lectka, T. Catalytic, asymmetric synthesis of β-lactams. J. Am. Chem. Soc. 2000, 122, 7831-7832.
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56. For another type of catalytic activation of the imine, see: France, S.; Shah, M. H.; Weatherwax, A.; Wack, H.; Roth, J. P.; Lectka, T. Bifunctional Lewis acid-nucleophile-based asymmetric catalysis: Mechanistic evidence for imine activation working in tandem with chiral enolate formation in the synthesis of β-lactams. J. Am. Chem. Soc. 2005, 127, 1206-1215.