443640-85-5Relevant 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
supporting information; experimental part, 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.
Reactivity of the lithium anion of the (S,S)-bis-p-tolylsulfinyl methane. A versatile synthesis of enantiopure alkylidene 1,1-bis-tolysulfoxides
Delouvrié, Bénédicte,Nájera, Francisco,Fensterbank, Louis,Malacria, Max
, p. 130 - 135 (2007/10/03)
We describe herein a new synthesis of enantiopure alkylidene 1,1-bis-p-tolyl-sulfoxides (5), based on a two-steps sequence. The first one involves the alkylation of the lithium anion of the (S,S)-bis-p-tolylsulfinylmethane (1) with aldehydes. The second one consists in a mild dehydration of the sulfinyl alcohols 3 and 4 with the morpho CDI reagent. Some features (reactivity, diastereoselectivity) of the alkylation reaction are discussed.
