期刊
SYNTHESIS-STUTTGART
卷 47, 期 7, 页码 992-1006出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0034-1379978
关键词
amino acids; cyclopropane; Grignard reaction; nitriles; titanium
资金
- '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'
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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