Asymmetric Titanium-Catalyzed Cyclopropanation of Nitriles with Grignard Reagents

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...

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Bibliographic Details
Published in:SynOpen (2017) 2018-01, Vol.2 (1), p.0041-0049
Main Authors: Caillé, Julien, Setzer, Paul, Boeda, Fabien, Pearson-Long, Morwenna S. M., Bertus, Philippe
Format: Article
Language:English
Subjects:
Chemical Sciences
cyclopropanes
enantioselectivity
grignard reagents
nitriles
Organic chemistry
spiro compounds
titanium
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Summary: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%).
ISSN:2509-9396
2509-9396
DOI:10.1055/s-0036-1591933