Journal
SYNLETT
Volume 31, Issue 6, Pages 575-580Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0039-1691570
Keywords
beta-lactams; allylic substitution; allylation; Lewis base catalysis
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Funding
- Carl-Zeiss-Stiftung (Carl-Zeiss Foundation)
- Friedrich-Schiller-Universitat Jena
- State of Thuringia
- Deutsche Bundesstiftung Umwelt (DBU) (German Environment Foundation) [20018/578]
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Enantioenriched beta-lactams are accessed via enantioselective allylation of anilines with Morita-Baylis-Hillman carbonates followed by a base-promoted cyclization. The resulting 3-methyleneazetidin-2-ones are amenable to diastereoselective functionalization to produce analogues of biologically active beta-lactams. The use of nearly equimolar quantities of the starting materials make this method efficient and straightforward.
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