A Fast Catalytic Asymmetric Aza‐Morita–Baylis–Hillman Reaction of N‐Sulfonated Imines with Methyl Vinyl Ketone in the Presence of Chiral Bifunctional Phosphane Lewis Bases
A Fast Catalytic Asymmetric Aza‐Morita–Baylis–Hillman Reaction of N‐Sulfonated Imines with Methyl Vinyl Ketone in the Presence of Chiral Bifunctional Phosphane Lewis Bases
复制标题
手性双功能膦路易斯碱存在下 N-磺化亚胺与甲基乙烯基酮的快速催化不对称 Aza-Morita-Baylis-Hillman 反应
DOI：
10.1002/ejoc.200800321
复制
发表时间：
2008
影响因子：
2.8
通讯作者：
M. Shi
中科院分区：
文献类型：
--
作者：
Zhi;Guangning Ma;M. Shi
设计并成功合成了一系列磷原子上含有一个苯基和一个给电子烷基的新型双功能手性膦Lewis碱。将这些双官能团的手性膦Lewis碱用于催化N-磺化亚胺与甲基乙烯基酮的不对称氮杂-森田-贝利斯-希尔曼反应，在室温下几小时内以良好到优异的产率和中等到良好的对映选择性得到了相应的加合物。据我们所知，这是迄今为止报道的最快的催化不对称MBH反应。(C)Wiley-VCH Verlag GmbH&Co.KGaA，69451，德国温海姆，2008年)。
A series of novel bifunctional chiral phosphane Lewis bases having one phenyl group and an electron-donating alkyl group on the phosphorus atom was designed and successfully synthesized. The use of these bifunctional chiral phosphane Lewis bases in catalytic asymmetric aza-Morita-Baylis-Hillman reactions (aza-MBH reactions) of N-sulfonated imines with methyl vinyl ketone affords the corresponding adducts in good-to-excellent yields and moderate-to-good enantioselectivities within a few hours at room temperature. To the best of our knowledge, this is the fastest catalytic asymmetric MBH reaction reported thus far. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).