Ávila Eloah P, Justo Rodrigo M S, Gonçalves Vanessa P, Pereira Adriane A, Diniz Renata, Amarante Giovanni W
Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
J Org Chem. 2015 Jan 2;80(1):590-4. doi: 10.1021/jo5024975. Epub 2014 Dec 12.
A highly diastereo- and enantioselective Mannich-type reaction of azlactones with aldimines catalyzed by a chiral phosphoric acid is described. Only 3 mol % catalyst was required to prepare the Mannich adducts in good yields with high stereochemical control (up to >19:1 dr, >99:1 er). Moreover, the final product contains two consecutive stereogenic centers, one of which is quaternary.
描述了在手性磷酸催化下，吖内酯与醛亚胺的高度非对映和对映选择性曼尼希型反应。仅需3 mol%的催化剂就能以高立体化学控制（高达>19:1的非对映体比例，>99:1的对映体比例）高产率制备曼尼希加合物。此外，最终产物含有两个连续的立体中心，其中一个是季碳中心。
