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Stereoselective formation of (Z)-2-fluoroalkenoates via Julia–Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones

Stereoselective formation of (Z)-2-fluoroalkenoates via Julia–Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones
Stereoselective formation of (Z)-2-fluoroalkenoates via Julia–Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones
The selective synthesis of fluoroalkenoates is reported from a pyrimidinyl fluorosulfone. This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia–Kocienski reaction is discussed.
0040-4020
5632-5639
Larnaud, Florent
b5b03dcb-6c7e-4232-8a38-4bf904805a18
Pfund, Emmanuel
ecfd6437-1953-4e22-9638-42d0d9f11bed
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Lequeux, Thierry
52eca0ba-760f-457b-9d61-52df125721b2
Larnaud, Florent
b5b03dcb-6c7e-4232-8a38-4bf904805a18
Pfund, Emmanuel
ecfd6437-1953-4e22-9638-42d0d9f11bed
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Lequeux, Thierry
52eca0ba-760f-457b-9d61-52df125721b2

Larnaud, Florent, Pfund, Emmanuel, Linclau, Bruno and Lequeux, Thierry (2014) Stereoselective formation of (Z)-2-fluoroalkenoates via Julia–Kocienski reaction of aldehydes with pyrimidinyl-fluorosulfones. Tetrahedron, 70 (35), 5632-5639. (doi:10.1016/j.tet.2014.06.081).

Record type: Article

Abstract

The selective synthesis of fluoroalkenoates is reported from a pyrimidinyl fluorosulfone. This sulfone allowed the preparation of Z-fluoroalkenoates with very high stereoselectivity from both aromatic and aliphatic aldehydes. The nature of the heterocycle on the course of the Julia–Kocienski reaction is discussed.

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Published date: 2 September 2014
Related URLs:
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow

Identifiers

Local EPrints ID: 368056
URI: http://eprints.soton.ac.uk/id/eprint/368056
DOI: doi:10.1016/j.tet.2014.06.081
ISSN: 0040-4020
PURE UUID: a47a2dfb-a1b0-47d9-a22a-b6744615db3d
ORCID for Bruno Linclau: ORCID iD orcid.org/0000-0001-8762-0170

Catalogue record

Date deposited: 09 Sep 2014 10:45
Last modified: 15 Mar 2024 03:05

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Contributors

Author: Florent Larnaud
Author: Emmanuel Pfund
Author: Bruno Linclau ORCID iD
Author: Thierry Lequeux

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