10140-30-4Relevant articles and documents
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Auer,E. et al.
, p. 802 - 806 (1967)
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Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates
Guasch, Joan,Díaz, Yolanda,Matheu, M. Isabel,Castillón, Sergio
, p. 7344 - 7347 (2014)
The reaction of dienyl carbamates with PhI(OR)2 in the presence of rhodium catalysts affords vinyl aziridines which are in situ regio- and stereoselectively opened to afford oxyamination products resulting from a selective SN2 (Rh2(OAc)4/PhI(OPiv)2) or SN2′ (Rh2(OPiv)4/PhI(OAc) 2) opening. The scope and limitations of this tandem process are described.
Chemo-, regio-, and stereoselective silver-catalyzed aziridination of dienes: Scope, mechanistic studies, and ring-opening reactions
Llaveria, Josep,Beltrán, álvaro,Sameera,Locati, Abel,Díaz-Requejo, M. Mar,Matheu, M. Isabel,Castillón, Sergio,Maseras, Feliu,Pérez, Pedro J.
supporting information, p. 5342 - 5350 (2014/05/06)
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 in high yields by means of the metal-mediated transfer of NTs (Ts = p-toluensulfonyl) units from PhI=NTs. The preferential aziridination occurs at the double bond neighboring to the hydroxyl end in ca. 9:1 ratios that assessed a very high degree of regioselectivity. The reaction with the silver-based catalysts proceeds in a stereospecific manner, i.e., the initial configuration of the C=C bond is maintained in the aziridine product (cis or trans). The degree of regioselectivity was explained with the aid of DFT studies, where the directing effect of the OH group of 2,4-diene-1-ols plays a key role. Effective strategies for ring-opening of the new aziridines, deprotection of the Ts group, and subsequent formation of β-amino alcohols have also been developed.
Synthesis of D/L-erythro-Sphingosine Using a Tethered Aminohydroxylation Reaction as the Key Step
Morales-Serna, Jose Antonio,Isabel Matheu, Yolanda Diaz M.,Castillon, Sergio
experimental part, p. 710 - 712 (2009/09/06)
A diastereoselective synthesis of racemic D/L-erythro- sphingosine is described. The approach involves employing tethered aminohydroxylation (TA) to introduce the 2-amino and 3- hydroxy functions with required stereochemistry. Georg Thieme Verlag Stuttgart.
