Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 23, Issue 2, Pages 268-272Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201604995
Keywords
organocatalysis; synergistic catalysis; synthetic methods; transition-metal catalysis; vinyl aziridines
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Funding
- Aarhus University
- Carlsberg Foundation
- FNU
- European Commission [PIEF-GA-2013-622413]
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The first asymmetric [3+2] cycloaddition of vinyl aziridines with alpha,beta-unsaturated aldehydes, based on synergistic catalysis, is disclosed. This methodology allows the formation of attractive pyrrolidine structures in good yields (up to 84%), moderate diastereoselectivity, and high enantioselectivity values (up to >99% ee). Additionally, a tricyclic pyrrolidine core structure found in biologically active molecules was synthesized in a one-pot fashion by using the presented reaction concept. Finally, a mechanistic proposal is outlined.
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