Brønsted Acid-Catalyzed Dehydrative Nazarov-Type Cyclization/C2–N1 Cleavage Cascade of Perfluoroalkylated 3-Indolyl(2-benzothienyl)methanols
Feng Li, Yuling Teng, Xiangdong Yu, Zeliang Wang, Weidong Rao
Abstract
-toluenesulfonic acid-catalyzed dehydrative Nazarov-type cyclization/C2-N1 bond cleavage cascade reaction of perfluoroalkylated 3-indolyl(2-benzothienyl)methanols has been developed. This reaction provides an efficient and practical protocol for the construction of highly functionalized benzothiophene-fused cyclopentenones with exclusive stereoselectivity. In addition, this cascade transformation also delineates a rare example of the involvement of the selective C2-N1 bond cleavage of indoles.
Topics & Concepts
ChemistryBenzothiopheneCatalysisCascadeCleavage (geology)Brønsted–Lowry acid–base theoryBond cleavageCascade reactionCombinatorial chemistryMedicinal chemistryStereochemistryStereoselectivityOrganic chemistryThiopheneFracture (geology)Geotechnical engineeringChromatographyEngineeringSynthesis of Indole DerivativesAxial and Atropisomeric Chirality SynthesisAsymmetric Synthesis and Catalysis