通过串联达参反应/半胺化反应实现α,β-环氧-γ-内酰胺的不对称合成。
Asymmetric Synthesis of α,β-Epoxy-γ-lactams through Tandem Darzens/Hemiaminalization Reaction.
作者信息
Shen Bin, Liu Wen, Cao Weidi, Liu Xiaohua, Feng Xiaoming
机构信息
Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , China.
出版信息
Org Lett. 2019 Jun 21;21(12):4713-4716. doi: 10.1021/acs.orglett.9b01589. Epub 2019 Jun 11.
A catalytic asymmetric tandem Darzens/hemiaminalization reaction of glyoxals with α-bromo-β-esteramides or α-bromo-β-ketoamide was accomplished in the presence of a chiral N,N'-dioxide/Yb(III) complex. Various chiral α,β-epoxy-γ-lactams were obtained in moderate to good yields with excellent diastereo- and enantioselectivities. The versatility of the transformation is illustrated in the formal synthesis of berkeleyamide D.
在手性N,N'-二氧化物/Yb(III)配合物存在下，实现了乙二醛与α-溴-β-酯酰胺或α-溴-β-酮酰胺的催化不对称串联Darzens/半胺化反应。以中等至良好的产率获得了各种手性α,β-环氧-γ-内酰胺，具有优异的非对映选择性和对映选择性。该转化的通用性在伯克利酰胺D的形式合成中得到了体现。
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