Aminocatalytic Asymmetric <i>exo</i>-Diels–Alder Reaction with Methiodide Salts of Mannich Bases and 2,4-Dienals to Construct Chiral Spirocycles
作者:Shan-Jun Zhang、Jun Zhang、Qing-Qing Zhou、Lin Dong、Ying-Chun Chen
DOI:10.1021/ol4002015
日期:2013.2.15
An asymmetric exo-Diels–Alder reaction of α-methylene carbonyl compounds, generated in situ from stable methiodide salts of Mannich bases, with 2,4-dienals, has been developed through trienamine activation of a chiral secondary amine. A spectrum of spirocyclanes with high molecular complexity was efficiently constructed in moderate to excellent diastereo- and enantioselectivity.
通过手性仲胺的三烯胺活化,已经开发出了由曼尼希碱的稳定甲硫盐与2,4-二苯胺原位生成的α-亚甲基羰基化合物的不对称exo -Diels-Alder反应。具有中等分子至非对映体和对映体选择性的高效分子结构的螺环化合物的光谱得到了有效构建。