Stereoselectivity of the Honda–Reformatsky reaction in reactions with ethyl bromodifluoroacetate with ?-oxygenated sulfinylimines
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. Excellent diastereoselectivities (>94:6) are obtained for the matched cases. In contrast, reaction with sulfinylimines derived from unsubstituted alkanals proceeded with virtually no diastereoselectivity
4186-4195
Fontenelle, Clément Q.
c746c5ea-96bc-46c2-849d-47215ab58c03
Conroy, Matthew
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Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Poisson, Thomas
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Pannecoucke, Xavier
00b4b2af-fb90-4bae-8ef0-c407b1aa1b41
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
2014
Fontenelle, Clément Q.
c746c5ea-96bc-46c2-849d-47215ab58c03
Conroy, Matthew
aa831580-885c-4f59-a8c9-5e7680d6c8b4
Light, Mark
cf57314e-6856-491b-a8d2-2dffc452e161
Poisson, Thomas
dd23a866-a9fd-4132-a386-9ddf9d0684e2
Pannecoucke, Xavier
00b4b2af-fb90-4bae-8ef0-c407b1aa1b41
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Fontenelle, Clément Q., Conroy, Matthew, Light, Mark, Poisson, Thomas, Pannecoucke, Xavier and Linclau, Bruno
(2014)
Stereoselectivity of the Honda–Reformatsky reaction in reactions with ethyl bromodifluoroacetate with ?-oxygenated sulfinylimines.
Journal of Organic Chemistry, 79 (9), .
(doi:10.1021/jo500396p).
Abstract
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
Text
Linclau Poisson manuscript_v3_revised.pdf
- Accepted Manuscript
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Published date: 2014
Additional Information:
This document is the unedited Author’s version of a Submitted Work that was subsequently accepted for publication in [JournalTitle], copyright © American Chemical Society after peer review.
Organisations:
Organic Chemistry: Synthesis, Catalysis and Flow
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Local EPrints ID: 364728
URI: http://eprints.soton.ac.uk/id/eprint/364728
ISSN: 0022-3263
PURE UUID: a844a692-2f42-402d-ba52-2dcf44a3cf4e
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Date deposited: 22 May 2014 07:44
Last modified: 15 Mar 2024 03:05
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Contributors
Author:
Clément Q. Fontenelle
Author:
Matthew Conroy
Author:
Thomas Poisson
Author:
Xavier Pannecoucke
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