title: Unprecedented one-pot, domino tertiary alcohol protection-Michael type addition of halides to Morita-Baylis-Hillman adduct of isatin with RCOX/K2CO3: diastereoselective synthesis of oxindole appended β-halo esters.
abstract: A facile method utilizing RCOX/K2CO3 as a novel reagent for conjugate addition of hydrogen halide, in addition to tertiary (3°)-hydroxyl protection that leads to the synthesis of functionalized β-halo Morita-Baylis-Hillman ester appended oxindoles, has been developed. The diastereoselective one-pot O-acylation-hydrohalogenation observed cannot otherwise be performed by treatment with hydrohalide. Deprotection of a 3°-hydroxyl protecting group has also been demonstrated by treatment with hydrochloric acid.
authors: Council of Scientific and Industrial Research-Central Leather Research Institute, Organic Chemistry Division, Adyar, Chennai-600020, India.
authors: Rajarethinam
authors: R
authors: Solaiselvi
authors: Ponnusamy
authors: P
authors: Shanmugam
authors: Asit Baran
authors: AB
authors: Mandal
mesh_terms: D002384:Catalysis; D004952:Esters; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D006851:Hydrochloric Acid / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007510:Isatin / Q000737:chemistry*; D015394:Molecular Structure; D000078183:Oxindoles; D013237:Stereoisomerism
chemical_list: D004952:Esters; D006846:Hydrocarbons, Halogenated; D007211:Indoles; D000078183:Oxindoles; C022960:2-oxindole; D007510:Isatin; D006851:Hydrochloric Acid