Highly diastereoselective addition of lithio vinyl sulfoxides to N-sulfinimines: an entry to enantiopure 3-sulfinyl-2,5-cis-dihydropyrroles.
The addition of enantiopure alpha-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 amines have been further transformed into highly functionalized 3-sulfinyl and 3-sulfonyl 2,5- cis-dihydropyrroles by reaction with electrophiles.
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Instituto de Química Orgánica General, CSIC, Juan de la Cierva 3, 28006 Madrid, Spain. iqov379@iqog.csic.es
Fernández de la Pradilla
Roberto
R
Ureña
Mercedes
M
Colomer
Ignacio
I