title: Cascade oxidative dearomatization/semipinacol rearrangement: an approach to 2-spirocyclo-3-oxindole derivatives.
abstract: A novel cascade reaction involving oxidative dearomatization/semipinacol rearrangement of indol-2-yl cyclobutanols is explored with N-sulfonyloxaziridine (Davis oxaziridines) as oxidant, generating various 2-spiroquaternary 3-oxindoles in modest to good yields. This method might be useful in the synthesis of indole-based alkaloids bearing 2-spiroquaternary carbon centers. PTS=p-toluenesulfonic acid monohydrate.
authors: State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P R China.
authors: Jin-Bao
authors: JB
authors: Peng
authors: Yue
authors: Y
authors: Qi
authors: Ai-Jun
authors: AJ
authors: Ma
authors: Yong-Qiang
authors: YQ
authors: Tu
authors: Fu-Min
authors: FM
authors: Zhang
authors: Shao-Hua
authors: SH
authors: Wang
authors: Shu-Yu
authors: SY
authors: Zhang
mesh_terms: D001388:Aziridines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003503:Cyclobutanes / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D000078183:Oxindoles; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001388:Aziridines; D003503:Cyclobutanes; D007211:Indoles; D000078183:Oxindoles; D013141:Spiro Compounds; C022960:2-oxindole