Asymmetric Organocatalytic 1,6-Conjugate Addition of <i>para-</i>Quinone Methides Using [1,2]-Phospha-Brook Rearrangement
Qingfa Tan, Ning Guo, Linhan Yang, Fei Wang, Xiaoming Feng, Xiaohua Liu
Abstract
Pudovik addition/[1,2]-phospha-Brook rearrangement as an efficient tool for generation of anionic nucleophiles is an attractive strategy for the construction of C–C bonds in organic synthesis. Herein, we report organocatalytic 1,6-conjugate addition of para -quinone methides utilizing Pudovik addition/[1,2]-phospha-Brook rearrangement. Chiral guanidine–sulfonamide catalyzed the three-component reaction efficiently, providing biologically active oxindole/biaryl/phosphorus-based structures in high yields with excellent diastereo- and enantioselectivities. A possible bifunctional catalytic mode was proposed to elucidate the chiral control of this process.
Topics & Concepts
BifunctionalOxindoleConjugateNucleophileOrganocatalysisChemistryGuanidineCombinatorial chemistryCatalysisQuinoneBifunctional catalystSulfonamideEnantioselective synthesisStereochemistryOrganic chemistryMathematicsMathematical analysisSynthesis of Indole DerivativesCarbohydrate Chemistry and SynthesisMulticomponent Synthesis of Heterocycles