Chemo-, regio-, and stereoselective silver-catalyzed aziridination of dienes: scope, mechanistic studies, and ring-opening reactions.
作者： Josep Llaveria , Álvaro Beltrán , W. M. C. Sameera , Abel Locati , M. Mar Díaz-Requejo
DOI: 10.1021/JA412547R
关键词: Stereoselectivity 、 Regioselectivity 、 Ring (chemistry) 、 Aziridine 、 Stereospecificity 、 Chemistry 、 Stereochemistry 、 Catalysis 、 Trispyrazolylborate 、 Double bond
摘要: Silver complexes bearing trispyrazolylborate ligands (Tpx) catalyze the aziridination of 2,4-diene-1-ols in a chemo-, regio-, and stereoselective manner to give vinylaziridines high yields by means metal-mediated transfer NTs (Ts = p-toluensulfonyl) units from PhI═NTs. The preferential occurs at double bond neighboring hydroxyl end ca. 9:1 ratios that assessed very degree regioselectivity. reaction with silver-based catalysts proceeds stereospecific manner, i.e., initial configuration C═C is maintained aziridine product (cis or trans). regioselectivity was explained aid DFT studies, where directing effect OH group plays key role. Effective strategies for ring-opening new aziridines, deprotection Ts group, subsequent formation β-amino alcohols have also been developed.
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