1070900-69-4Relevant academic research and scientific papers
An approach to the stereoselective synthesis of enantiopure dihydropyrroles and aziridines from a common sulfinyl-sulfinamide intermediate
Viso, Alma,Fernandez De La Pradilla, Roberto,Urena, Mercedes,Bates, Robert H.,Del Aguila, Miguel A.,Colomer, Ignacio
experimental part, p. 525 - 542 (2012/03/22)
The diastereoselective addition of lithiated vinyl sulfoxides to enantiopure sulfinimines provides direct access to a wide assortment of allylic sulfinamides in good yields and excellent selectivities. These adducts are key precursors to differently functionalized cis- and trans-dihydropyrroles. Modulation of the protecting group on nitrogen prior to cyclization has a significant impact on the stereochemical outcome, allowing for the selective preparation of 2,5-cis- or 2,5-trans-3-sulfinyl disubstituted dihydropyrroles from a common sulfinamide intermediate. Further research on halocyclization conditions has also yielded a stereoselective synthesis of trisubstituted vinyl aziridines from these chiral sulfinamides, simply by changing the halogenating agent.
Highly diastereoselective addition of lithio vinyl sulfoxides to N-sulfinimines: An entry to enantiopure s-sulfinyl-2-5-cis-dihydropyrroles
Viso, Alma,De La Pradilla, Roberto Fernandez,Urena, Mercedes,Colomer, Ignacio
supporting information; experimental part, p. 4775 - 4778 (2009/06/05)
(Chemical Equation Presented The addition of enantiopure α-metalated vinyl and dienyl sulfoxides to enantiomerically pure N-sulfinimines takes place with high diastereoselectivity primarily directed by the N-sulfinimine sulfur. The resulting allylic amine
