Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with ?-oxygenated sulfinylimines

The Reformatsky reaction of ethyl bromodifluoroacetate to ?-oxygenated sulfinylimines is described. Using Honda-Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Exce...

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Bibliographic Details
Main Authors: Fontenelle, Clément Q. (Author), Conroy, Matthew (Author), Light, Mark (Author), Poisson, Thomas (Author), Pannecoucke, Xavier (Author), Linclau, Bruno (Author)
Format: Article
Language:English
Published: 2014.
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Online Access:Get fulltext
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042 |a dc 
100 1 0 |a Fontenelle, Clément Q.  |e author 
700 1 0 |a Conroy, Matthew  |e author 
700 1 0 |a Light, Mark  |e author 
700 1 0 |a Poisson, Thomas  |e author 
700 1 0 |a Pannecoucke, Xavier  |e author 
700 1 0 |a Linclau, Bruno  |e author 
245 0 0 |a Stereoselectivity of the Honda-Reformatsky reaction in reactions with ethyl bromodifluoroacetate with ?-oxygenated sulfinylimines 
260 |c 2014. 
856 |z Get fulltext  |u https://eprints.soton.ac.uk/364728/1/Linclau%2520Poisson%2520manuscript_v3_revised.pdf 
520 |a The Reformatsky reaction of ethyl bromodifluoroacetate to ?-oxygenated sulfinylimines is described. Using Honda-Reformatsky conditions, the reaction proceeds with double diastereodifferentiation, with the configuration of the sulfinyl group determining the stereochemical course of the reaction. Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity 
540 |a cc_by_nc_4 
655 7 |a Article