Base-enabled access to diastereoselective spirofuran oxindoles and γ-functionalized allenoates
化学
组合化学
催化作用
表面改性
基础(拓扑)
奥西多尔
区域选择性
有机催化
亲核细胞
环加成
作者
Basavaraja D,M S Ajay Krishna,Jagadeesh Krishnan,C S Athira,R R Amrutha,Eringathodi Suresh,Sasidhar B. Somappa
出处
期刊:Chemical Communications [The Royal Society of Chemistry] 日期:2021-02-19卷期号:57 (14): 1746-1749
标识
DOI:10.1039/d0cc07715a
摘要
Base assisted divergent reactivity of isatins and allenoates has been achieved, which afforded diastereoselective spirofuran oxindoles and γ-functionalized allenoates. The DBU mediated Morita–Baylis–Hillman (MBH) reaction followed by the cascade annulation through the stabilized β-ammonium enolate intermediate led to the spiro-framework, wherein DABCO furnished the γ-functionalized allenoates. The protocol offers access to biologically relevant functionalized oxindole scaffolds with an excellent substrate scope under mild reaction conditions.