Bridged-Type Selective Intramolecular Nitrone-Alkene Cycloaddition: Computational Chemistry-Inspired Regioselectivity
Tanawat Phumjan1, Tomohiro Yazawa1, Shinji Harada1,2
1Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1 Inohana, Chuo-ku, Chiba 260-8675, Japan.
Abstract:
A regioselective intramolecular nitrone-alkene cycloaddition for synthesizing oxazabicyclo ring-fused indoles is reported. Computational studies guided the development of optimal conditions using In(OTf)3 as a Lewis acidic reagent. This method demonstrates a broad substrate scope, forming seven- and eight-membered carbocycles with various substituents, and provides a versatile route to complex nitrogen-containing scaffolds with potential applications in medicinal chemistry and the total synthesis of biologically active compounds.
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