手性布朗斯特酸催化的恶唑烷酮与醛亚胺的立体选择性曼尼希型反应。
Chiral brønsted Acid-catalyzed stereoselective Mannich-type reaction of azlactones with aldimines.
作者信息
Ávila Eloah P, Justo Rodrigo M S, Gonçalves Vanessa P, Pereira Adriane A, Diniz Renata, Amarante Giovanni W
机构信息
Chemistry Department, Federal University of Juiz de Fora, Cidade Universitária Martelos, Martelos, Juiz de Fora, MG, Brazil 36036-900.
出版信息
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。
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