Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 18, Pages 3307-3312Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100432
Keywords
asymmetric synthesis; catalysis; cycloaddition; organocatalysis; pyrrolidines
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Funding
- University of the Basque Country UPV/EHU
- Spanish MICINN [CTQ2008-00136/BQU]
- Diputacion Foral de Bizkaia/Bizkaiko Foru Aldundia [DIPE08/03]
- Basque Government [Grupos IT-328-10]
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Racemic alpha-iminocyanoacetates have been used as azomethine ylide precursors in the catalytic enantioselective [3+2]cycloaddition with alpha,beta-unsaturated aldehydes catalyzed by (S)-alpha,alpha-diphenylprolinol leading to the fully stereocontrolled formation of pyrrolidine cycloadducts with four stereocentres, one of them being a quaternary one. The reaction proceeded with excellent yields, endo-selectivities and enantioselectivities. Remarkably, complete 2,5-diastereoselection has also been achieved under the optimized reaction conditions, which has been explained in terms of the participation of intramolecular H-bonding interaction which contributes to stabilize one determined geometry for the in situ generated azomethine ylide.
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