Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions

Guillaume Vincent; Saloua Cheli; Rocio Martinez Mallorquin; Adi Abramovitch; Sophie Beauviere; Catherine Gomez; Franck Brebion; Ilan Marek; Max Malacria; Jean Philippe Goddard; Louis Fensterbank

doi:10.1016/j.crci.2015.11.012

Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions

Guillaume Vincent, Saloua Cheli, Rocio Martinez Mallorquin, Adi Abramovitch, Sophie Beauviere, Catherine Gomez, Franck Brebion, Ilan Marek, Max Malacria, Jean Philippe Goddard, Louis Fensterbank

Technion - Israel Institute of Technology

Research output: Contribution to journal › Article › peer-review

Abstract

[1,4]-additions of various nucleophiles such as lithiated carbamates, alkoxides or ester enolates onto enantiopure alkylidene bis-sulfoxides proceed with high diastereoselectivity. The oxidation of the resulting carbanions with iron(III) salts induces the radical cyclizations onto alkenes with a high diastereoselectivity leading to enantiopure carbo- or heterocycles. Moreover, allylic radicals have been generated by deprotonation or [1,6]-conjugate addition from alkylidene bis-sulfoxides followed by oxidation.

Original language	English
Pages (from-to)	403-411
Number of pages	9
Journal	Comptes Rendus Chimie
Volume	19
Issue number	3
DOIs	https://doi.org/10.1016/j.crci.2015.11.012
State	Published - 1 Mar 2016

Keywords

Alkylidene bis-sulfoxide
Conjugate addition
Radical
Red-ox
Tandem

All Science Journal Classification (ASJC) codes

General Chemistry
General Chemical Engineering

Access to Document

10.1016/j.crci.2015.11.012

Cite this

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title = "Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions",

abstract = "[1,4]-additions of various nucleophiles such as lithiated carbamates, alkoxides or ester enolates onto enantiopure alkylidene bis-sulfoxides proceed with high diastereoselectivity. The oxidation of the resulting carbanions with iron(III) salts induces the radical cyclizations onto alkenes with a high diastereoselectivity leading to enantiopure carbo- or heterocycles. Moreover, allylic radicals have been generated by deprotonation or [1,6]-conjugate addition from alkylidene bis-sulfoxides followed by oxidation.",

keywords = "Alkylidene bis-sulfoxide, Conjugate addition, Radical, Red-ox, Tandem",

author = "Guillaume Vincent and Saloua Cheli and Mallorquin, \{Rocio Martinez\} and Adi Abramovitch and Sophie Beauviere and Catherine Gomez and Franck Brebion and Ilan Marek and Max Malacria and Goddard, \{Jean Philippe\} and Louis Fensterbank",

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doi = "10.1016/j.crci.2015.11.012",

language = "الإنجليزيّة",

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T1 - Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions

AU - Vincent, Guillaume

AU - Cheli, Saloua

AU - Mallorquin, Rocio Martinez

AU - Abramovitch, Adi

AU - Beauviere, Sophie

AU - Gomez, Catherine

AU - Brebion, Franck

AU - Marek, Ilan

AU - Malacria, Max

AU - Goddard, Jean Philippe

AU - Fensterbank, Louis

PY - 2016/3/1

Y1 - 2016/3/1

N2 - [1,4]-additions of various nucleophiles such as lithiated carbamates, alkoxides or ester enolates onto enantiopure alkylidene bis-sulfoxides proceed with high diastereoselectivity. The oxidation of the resulting carbanions with iron(III) salts induces the radical cyclizations onto alkenes with a high diastereoselectivity leading to enantiopure carbo- or heterocycles. Moreover, allylic radicals have been generated by deprotonation or [1,6]-conjugate addition from alkylidene bis-sulfoxides followed by oxidation.

AB - [1,4]-additions of various nucleophiles such as lithiated carbamates, alkoxides or ester enolates onto enantiopure alkylidene bis-sulfoxides proceed with high diastereoselectivity. The oxidation of the resulting carbanions with iron(III) salts induces the radical cyclizations onto alkenes with a high diastereoselectivity leading to enantiopure carbo- or heterocycles. Moreover, allylic radicals have been generated by deprotonation or [1,6]-conjugate addition from alkylidene bis-sulfoxides followed by oxidation.

KW - Alkylidene bis-sulfoxide

KW - Conjugate addition

KW - Radical

KW - Red-ox

KW - Tandem

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DO - 10.1016/j.crci.2015.11.012

M3 - مقالة

SN - 1631-0748

VL - 19

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EP - 411

JO - Comptes Rendus Chimie

JF - Comptes Rendus Chimie

IS - 3

ER -

Oxidation of bis-sulfinyl carbanions as the pivot of ionic/radical tandem reactions

Abstract

Keywords

All Science Journal Classification (ASJC) codes

Access to Document

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