4.5 Article

Titanium-Mediated Cyclopropanation of Nitriles with Unsaturated Grignard Reagents: Application to the Synthesis of Constrained Lysine Derivatives

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

  1. 'Agence Nationale de la Recherche' (ANR) [BLAN07-2_194466]
  2. 'Centre National de la Recherche Scientifique'
  3. 'Region Pays-de-la-Loire'
  4. 'Ministere de l'Enseignement Superieur et de la Recherche'

向作者/读者索取更多资源

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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