An anionic nucleophilic catalyst system for the diastereoselective synthesis of trans-β-lactams

Organic Letters

Volumn 7, Issue 16, 2005, Pages 3461-3463

  Weatherwax, Anthony ^a   Abraham, Ciby J ^a   Lectka, Thomas ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BETA LACTAM;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ANIONS; BETA-LACTAMS; CATALYSIS; CYCLIZATION; STEREOISOMERISM;

EID: 23944510158     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0511070     Document Type: Article

References (17)

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14. Change in diastereoselectivity can be termed a "switch mechanism" (wherein a change in the nature of the catalyst affords a dramatically different reaction outcome for the same reacting partners), a long-standing interest of ours. For example, see: Ferraris, D.; Drury, W. J., III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568-4569.
15. Such a system appears to be unique, the closest analogy evident in the literature, although not strictly applicable, can be seen in: Ritchie, C. D.; Hofelich, T. C. J. Am. Chem. Soc. 1980, 102, 7039-7044.
16. This mechanistic hypothesis can be thought of as a specific example of the more general phenomenon of ion aggregation and the role that it may be playing in the diastereoselectivity of the reaction.
17. Epimerization can conceivably occur through proton abstraction on the formed β-lactam product, either at the α- or β-positions. However, another plausible mechanism involves the epimerization of the acidified α-proton on a ring-opened acylammonium intermediate. Further study should differentiate between these possibilities.