RT Journal Article
T1 Highly Diastereoselective [3 2] Cycloadditions between Nonracemic p-Tolylsulfinimines and Iminoesters:An Efficient Entry to Enantiopure Imidazolidines and Vicinal Diaminoalcohols
A1 Viso Beronda, Alma
A1 Fernández de la Pradilla, Roberto
A1 García Suárez, Ana Beatriz
A1 Guerrero-Strachan, Carlos
A1 Alonso Rodríguez, Marta Isabel
A1 Tortosa Manzanares, Mariola
A1 Flores Aguilar-Amat, Aída
A1 Martínez-Ripoll, Martín
A1 Fonseca Ruiz, Isabel
A1 André, Isabelle
A1 Rodríguez Fernández-Pacheco, Ana María
AB A new procedure for the asymmetric synthesis of imidazolidines and vicinal diamines is reported. The 1,3-dipolar cycloaddition between nonracemic p-tolylsulfinimines and azomethine ylides generated in situ from α-iminoesters and LDA produces N-sulfinylimidazolidines with a high degree of stereocontrol. In contrast, the presence of Lewis acids promotes formation of the cycloadducts through a highly diastereoselective process with opposite stereochemistry. Subsequent transformations of the imidazolidines including oxidative, reductive, and hydrolytic processes that provide easy access to vicinal diaminoalcohols have been explored. Among these, reductive cleavage of the aminal with LiAlH4 is an extremely efficient and general reaction for the synthesis of enantiopure N-sulfinyl-N′-benzyldiaminoalcohols.
PB Wiley
YR 2003
FD 2003-06-06
LK https://hdl.handle.net/20.500.14352/98462
UL https://hdl.handle.net/20.500.14352/98462
LA eng
NO Madrid Ciencia y Tecnología
NO Comunidad de Madrid
DS Docta Complutense
RD 29 jun 2025