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Synthesis 2018; 50(10): 1973-1978
DOI: 10.1055/s-0037-1609434
DOI: 10.1055/s-0037-1609434
paper
Synthesis of 2-Azabicyclo[n.2.0]alkane-Derived Building Blocks
The work was supported by Enamine Ltd.
Weitere Informationen
Publikationsverlauf
Received: 05. Januar 2018
Accepted after revision: 26. Februar 2018
Publikationsdatum:
29. März 2018 (online)
Abstract
An approach to 2-azabicyclo[n.2.0]alkane derivatives (n = 1, 2), which relies on a tandem Strecker reaction–intramolecular nucleophilic cyclization (STRINC) sequence of the corresponding 2-(ω-chloroalkyl)cyclobutanones (in turn prepared by [2+2] cycloaddition of keteniminium salts and ethylene) is described. The utility of the method is demonstrated by multigram syntheses of bicyclic proline analogues, monoprotected diamines, as well as parent 2-azabicyclo[4.2.0]octane.
Key words
cycloaddition - bicyclic compounds - amino acids - conformational restriction - cyclobutanes - nitrogen heterocycles - keteniminium salts - Strecker reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609434.
- Supporting Information
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