Journal
SYNTHESIS-STUTTGART
Volume 47, Issue 7, Pages 992-1006Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1379978
Keywords
amino acids; cyclopropane; Grignard reaction; nitriles; titanium
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Funding
- 'Agence Nationale de la Recherche' (ANR) [BLAN07-2_194466]
- 'Centre National de la Recherche Scientifique'
- 'Region Pays-de-la-Loire'
- 'Ministere de l'Enseignement Superieur et de la Recherche'
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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.
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