1236384-44-3Relevant academic research and scientific papers
Chiral bisguanidine-catalyzed inverse-electron-demand hetero-diels-alder reaction of chalcones with azlactones
Dong, Shunxi,Liu, Xiaohua,Chen, Xiaohong,Mei, Fang,Zhang, Yulong,Gao, Bo,Lin, Lili,Feng, Xiaoming
supporting information; experimental part, p. 10650 - 10651 (2010/11/04)
A new type of C2-symmetric chiral bisguanidine was designed as a highly efficient catalyst in the inverse-electron-demand hetero-Diels-Alder reaction of chalcones with azlactones for the first time. A wide variety of γ, I-unsaturated I-lactone derivatives with α-quaternary-ss- tertiary stereocenters were obtained in high yields (up to 88%) with excellent enantioselectivities (up to 99% ee). Hydrogen bonds were considered to be crucial for the activation and stereoinduction of the reaction. In all cases, the major was HDA adducts, which were obtained as a single diastereomer along with little amount of Michael addition products.
