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- Title
Lewis Acid-Catalyzed [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and Enamines: Enantioselective Synthesis of Nitrogen-Functionalized Cyclopentane Derivatives.
- Authors
Verma, Kamal; Banerjee, Prabal
- Abstract
A straightforward and efficient method for the synthesis of nitrogen-functionalized cyclopentane derivatives via [3+2] cycloaddition of enamines with donor-acceptor cyclopropanes in the presence of catalytic amounts of various Lewis acids at room temperature has been developed; furthermore, the corresponding β-amino acid was synthesized by monodecarboxylation and hydrogenolysis. An enantioenriched synthesis of nitrogen-functionalized cyclopentane derivatives through dynamic kinetic asymmetric transformation of racemic donor-acceptor cyclopropanes has also been achieved employing a copper complex [Cu(OTf)2- L1] as the catalyst affording an enantiomeric ratio up to 8:1.
- Subjects
CYCLOPENTANE derivatives; NITROGEN; RING formation (Chemistry); ENAMINES; LEWIS acids; ENANTIOSELECTIVE catalysis
- Publication
Advanced Synthesis & Catalysis, 2016, Vol 358, Issue 13, p2053
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201600221