Lewis Acid-Catalyzed [3+2] Cycloaddition of Donor-Acceptor Cyclopropanes and Enamines: Enantioselective Synthesis of Nitrogen-Functionalized Cyclopentane Derivatives

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 corr...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2016-06, Vol.358 (13), p.2053-2058
Main Authors: Verma, Kamal, Banerjee, Prabal
Format: Article
Language:English
Subjects:
Asymmetry
Catalysis
Catalysts
Cycloaddition
Derivatives
donor-acceptor cyclopropanes
enamines
nitrogen-functionalized cyclopentanes
Organic compounds
Synthesis
Transformations
β-amino acids
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Summary: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.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201600221