Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
Division of Chemistry & Biological Chemistry, School of Physical & Mathematical Sciences, Nanyang Technological University, Singapore 637371.
Org Lett. 2020 Apr 3;22(7):2595-2599. doi: 10.1021/acs.orglett.0c00533. Epub 2020 Mar 19.
A NHC-promoted cascade reaction between β-methyl enal and dienone is developed for quick access to multicyclic lactone molecules bearing quaternary chiral carbon centers. Our study constitutes the first 1,6-addition of the acylazolium vinyl enolate γ-carbon via NHC catalysis and provides rapid access to complex lactone molecules that are otherwise difficult to prepare. The structurally sophisticated lactone products bearing up to four fused ring structures are afforded in up to quantitative yields with good to excellent enantioselectivities.
NHC 促进的β-甲基烯醛和二烯酮的级联反应被开发出来，用于快速获得含有季手性碳原子的多环内酯分子。我们的研究代表了通过 NHC 催化的酰基唑啉乙烯基烯醇盐γ-碳的首次 1,6-加成，并提供了快速获得复杂内酯分子的途径，否则这些内酯分子很难制备。具有多达四个稠合环结构的结构复杂的内酯产物以良好到优异的对映选择性定量收率得到。
