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CC BY ND NC 4.0 · SynOpen 2018; 02(01): 0041-0049
DOI: 10.1055/s-0036-1591933
DOI: 10.1055/s-0036-1591933
paper
Asymmetric Titanium-Catalyzed Cyclopropanation of Nitriles with Grignard Reagents
Autor*innen
J.C. and P.S. gratefully thank the ‘Ministère de l’enseignement supérieur et de la recherche‘, the ‘Centre National de la Recherche Scientifique’ and the ‘Région Pays-de-la-Loire’ for PhD fellowships.
Weitere Informationen
Publikationsverlauf
Received: 12. Dezember 2017
Accepted: 20. Januar 2018
Publikationsdatum:
20. Februar 2018 (online)
Abstract
The titanium-catalyzed asymmetric cyclopropanation of cyanoesters with Grignard reagents was investigated for the first time. Particularly, the study of the efficiency of Taddol-based titanium complexes has shown that the prior preparation of Taddol titanium complexes was not required and a large panel of ligands was evaluated by using this approach. The spirocyclopropanelactams were obtained with good diastereoselectivity and with moderate enantioselectivities from the main diastereoisomer (up to 32%).
Key words
cyclopropanes - enantioselectivity - Grignard reagents - nitriles - spiro compounds - titaniumSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0036-1591933.
- Supporting Information (PDF) (opens in new window)
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Reviews:
An alternative mechanism involving titanium ate complexes as proposed by Kulinkovich is also possible (and probable), but was not presented here to avoid overloading schemes. See: