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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
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
0022-3263
4186-4195
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.
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), 4186-4195. (doi:10.1021/jo500396p).

Record type: Article

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

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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
ORCID for Clément Q. Fontenelle: ORCID iD orcid.org/0000-0002-1630-3407
ORCID for Mark Light: ORCID iD orcid.org/0000-0002-0585-0843
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

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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 ORCID iD
Author: Matthew Conroy
Author: Mark Light ORCID iD
Author: Thomas Poisson
Author: Xavier Pannecoucke
Author: Bruno Linclau ORCID iD

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