An Efficient and Straightforward Access to Sulfur Substituted [2.2]Paracyclophanes: Application to Stereoselective Sulfenate Salt Alkylation

Jean-François Lohier; Florian Foucoin; Paul-Alain Jaffres; José I. Garcia; Jana Sopkova-de Oliveira Santos; Stéphane Perrio; Patrick Metzner

doi:10.1021/ol800161m

Journal articles

An Efficient and Straightforward Access to Sulfur Substituted [2.2]Paracyclophanes: Application to Stereoselective Sulfenate Salt Alkylation

Jean-François Lohier ¹ Florian Foucoin ¹ Paul-Alain Jaffres ² José I. Garcia ³ Jana Sopkova-de Oliveira Santos ⁴ Stéphane Perrio ¹ Patrick Metzner ⁴

1 LCMT - Laboratoire de chimie moléculaire et thioorganique

2 CEMCA - Chimie, Electrochimie Moléculaires et Chimie Analytique

3 ICMA-CSIC - Instituto de Ciencia de Materiales de Aragón [Saragoza, España]

4 CERMN - Centre d'Etudes et de Recherche sur le Médicament de Normandie

Abstract : A straightforward and high-yielding access to various [2.2]paracyclophanes possessing a sulfur-based functional group is reported, the key step being a SEAr reaction mediated by a sulfonium salt. The versatility of the methodology was exemplified by an original application in sulfenate salt chemistry, from which a remarkable chirality transfer was observed.

Document type :

Journal articles

Domain :

Chemical Sciences / Organic chemistry

Chemical Sciences

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https://hal.univ-brest.fr/hal-01580460
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Submitted on : Friday, September 1, 2017 - 3:26:20 PM
Last modification on : Friday, September 11, 2020 - 3:00:03 PM

An Efficient and Straightforward Access to Sulfur Substituted [2.2]Paracyclophanes: Application to Stereoselective Sulfenate Salt Alkylation

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An Efficient and Straightforward Access to Sulfur Substituted [2.2]Paracyclophanes: Application to Stereoselective Sulfenate Salt Alkylation

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