Diastereoselective [3 + 2] vs [4 + 2] Cycloadditions of Nitroprolinates with α,β-Unsaturated Aldehydes and Electrophilic Alkenes: An Example of Total Periselectivity

• Published in: Journal of organic chemistry Vol. 82; no. 12; pp. 6298 - 6312
• Main Authors: Selva, Verónica, Larrañaga, Olatz, Castelló, Luis M, Nájera, Carmen, Sansano, José M, de Cózar, Abel
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 16.06.2017; Amer Chemical Soc
• Subjects: Chemistry; Chemistry, Organic; Physical Sciences; Science & Technology; DENSITY FUNCTIONALS; L-PROLINE; ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; AZOMETHINE YLIDES; DIVERSITY; EFFICIENT; CATALYSTS; PYRROLIZIDINE DERIVATIVES; ALKALOIDS

Diastereoselective multicomponent reactions of enantioenriched 4-nitroprolinates, obtained by enantiocatalyzed 1,3-dipolar cycloaddition (1,3-DC) of imino esters and nitroalkenes, with α,β-unsaturated aldehydes and electrophilic alkenes proceed with total periselectivity depending on the structure o...