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Beilstein J. Org. Chem. 2014, 10, 1114–1120, doi:10.3762/bjoc.10.110
Graphical Abstract
Figure 1: Glutamate receptor ligands.
Scheme 1: Proposed synthetic plan for the preparation of compound of type Ib.
Scheme 2: Synthesis of 3-azetidinone derivative 16.
Scheme 3: Synthetic routes to prepare target cyclopropyl derivatives 20. Reagents and conditions: a) (EtO)2PO...
Figure 2: Mechanism for the attack of the carbene intermediate to the olefin moiety 18.
Figure 3: Representation of the lowest energy conformation of each diastereoisomers.
Scheme 4: Synthesis of glutamate “frozen” analogues 4-carboxy-1-(ethoxycarbonyl)-5-azaspiro[2.3]hexane.