TY - JOUR A1 - Martín-Rodríguez, María A1 - Castelló, Luis M. A1 - Nájera, Carmen A1 - Sansano, José M. A1 - Larrañaga, Olatz A1 - de Cózar, Abel A1 - Cossío, Fernando P. T1 - Synthetic scope and DFT analysis of the chiral binap–gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes JF - Beilstein Journal of Organic Chemistry PY - 2013/// VL - 9 SP - 2422 EP - 2433 SN - 1860-5397 DO - 10.3762/bjoc.9.280 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.9.280 KW - asymmetric catalysis KW - DFT KW - 1,3-dipolar cycloaddition KW - gold catalysis KW - NICS KW - NTR KW - oxazolones KW - prolines N2 - The 1,3-dipolar cycloaddition between glycine-derived azlactones with maleimides is efficiently catalyzed by the dimeric chiral complex [(Sa)-Binap·AuTFA]2. The alanine-derived oxazolone only reacts with tert-butyl acrylate giving anomalous regiochemistry, which is explained and supported by Natural Resonance Theory and Nucleus Independent Chemical Shifts calculations. The origin of the high enantiodiscrimination observed with maleimides and tert-butyl acrylate is analyzed using DFT computed at M06/Lanl2dz//ONIOM(b3lyp/Lanl2dz:UFF) level. Several applications of these cycloadducts in the synthesis of new proline derivatives with a 2,5-trans-arrangement and in the preparation of complex fused polycyclic molecules are described. ER - TY - JOUR AU - Nájera, C. AU - Sansano, J. M. JF - Chem. Rev. PY - 2007/// VL - 107 SP - 4584 EP - 4671 DO - 10.1021/cr050580o ER - TY - JOUR AU - Fisk, J. S. AU - Mosey, R. A. AU - Tepe, J. J. JF - Chem. Soc. Rev. PY - 2007/// VL - 36 SP - 1432 EP - 1440 DO - 10.1039/b511113g ER - TY - JOUR AU - Hewlett, N. M. AU - Hupp, C. D. AU - Tepe, J. J. 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