647835-10-7Relevant academic research and scientific papers
Conjugate additions to alkylidene bis(sulfoxides)
Brebion, Franck,Vincent, Guillaume,Chelli, Saloua,Kwasnieski, Ophelie,Najera, Francisco,Delouvrie, Benedicte,Marek, Ilan,Derat, Etienne,Goddard, Jean-Philippe,Malacria, Max,Fensterbank, Louis
, p. 1825 - 1833 (2012/02/01)
A general study on the conjugate addition of anionic nucleophiles to alkylidene bis(sulfoxides) is presented. Alkoxides gave high yielding and diastereoselective addition reactions, which could be influenced by solvents and the counteranion. Azides provided an interesting entry into sulfinyl-substituted triazoles. Organometallics, mainly copper reagents, proved also to be valuable nucleophiles, and complete inversion of the stereoselectivity was achieved in the addition reaction with the latter. Modelizations provide a rationale for the observed diastereoselectivity. Taking the Michael: Alkylidene bis(sulfoxides) are exquisite Michael acceptors toward a broad series of nucleophiles, and in most cases the reaction affords the adducts in high yields with complete diastereoselectivity.
Diastereoselective synthesis of enantiopure acyclic ss,ss -disubstituted vinylsulfoxides
Brebion, Franck,Goddard, Jean-Philippe,Fensterbank, Louis,Malacria, Max
supporting information; experimental part, p. 1917 - 1920 (2009/04/18)
Thermal elimination of sulfenic acid from enantiopure ss,ss -disubstituted bis-sulfoxides allows the stereoselective synthesis of enantiopure acyclic ss,ss -disubstituted vinylsulfoxides. This mild and stereospecific synthesis provides either (E) or (Z) v
Highly Diastereoselective Conjugate Addition to Alkylidene Bis(Sulfoxides): Asymmetric Synthesis of (+)-erythro-Roccellic Acid
Brebion, Franck,Delouvrie, Benedicte,Najera, Francisco,Fensterbank, Louis,Malacria, Max,Vaissermann, Jacqueline
, p. 5342 - 5345 (2007/10/03)
Facial stereocontrol is possible in Michael additions of nucleophiles (Nu) to alkylidene bis(sulfoxides), which proceed via nonchelated (A) or chelated (B) intermediates depending on the addition of an appropriate Lewis acid (LA). This intriguing reactivi
