CC BY ND NC 4.0 · SynOpen 2018; 02(01): 0041-0049
DOI: 10.1055/s-0036-1591933
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Asymmetric Titanium-Catalyzed Cyclopropanation of Nitriles with Grignard Reagents

Julien Caillé
,
Paul Setzer
,
Fabien Boeda
,
Morwenna S. M. Pearson-Long
,
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.
Further Information

Publication History

Received: 12 December 2017

Accepted: 20 January 2018

Publication Date:
20 February 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%).

Supporting Information

 
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