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Synthesis 2015; 47(07): 992-1006
DOI: 10.1055/s-0034-1379978
DOI: 10.1055/s-0034-1379978
paper
Titanium-Mediated Cyclopropanation of Nitriles with Unsaturated Grignard Reagents: Application to the Synthesis of Constrained Lysine Derivatives
Further Information
Publication History
Received: 18 November 2014
Accepted after revision: 15 December 2014
Publication Date:
28 January 2015 (online)
Abstract
A comparative study of the titanium-mediated cyclopropanation of (benzyloxy)acetonitrile and Boc-protected cyanohydrin using unsaturated Grignard reagents (but-3-enyl- and pent-4-enylmagnesium bromides) is described. The best conditions to provide the cis and trans isomers of cyclopropylamines bearing unsaturation were identified and the alkene moiety was subjected to chemical modifications, as shown by the synthesis of orthogonally protected cis- and trans-2,3-methanolysine, cis-2,3-methanoornithine, and cis-2,3-methanohomolysine.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379978.
- Supporting Information