84801-07-0Relevant articles and documents
Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers
Berhane, Ilyas A.,Burde, Ameya S.,Chemler, Sherry R.,Kennedy-Ellis, Jonathan J.,Zurek, Eva
supporting information, p. 10099 - 10102 (2021/10/06)
The enantioselective copper-catalyzed oxidative coupling of alkenols with styrenes for the construction of dihydropyrans, isochromans, pyrans and morpholines is reported. A concise formal synthesis of a σ1receptor ligand using this alkene carbo
Synthesis of Tetrahydroisoquinolines through an Iron-Catalyzed Cascade: Tandem Alcohol Substitution and Hydroamination
Marcyk, Paul T.,Cook, Silas P.
supporting information, p. 6741 - 6744 (2019/09/07)
Rapid assembly of saturated nitrogen heterocycles - the synthetically more challenging variants of their aromatic relatives - can expedite the synthesis of biologically relevant molecules. Starting from a benzylic alcohol tethered to an unactivated alkene, an iron-catalyzed tandem alcohol substitution and hydroamination provides access to tetrahydroisoquinolines in a single synthetic step. Using a mild iron-based catalyst, the combination of these operations forms two carbon-nitrogen bonds and provides a unique annulation strategy to access this valuable core.
Indium Catalyzed Hydrofunctionalization of Styrene Derivatives Bearing a Hydroxy Group with Organosilicon Nucleophiles
Kita, Yuji,Yata, Tetsuji,Nishimoto, Yoshihiro,Yasuda, Makoto
, p. 740 - 753 (2018/01/28)
Hydrofunctionalization is one of the most important transformation reactions of alkenes. Herein, we describe the development of an indium-triiodide-catalyzed hydrofunctionalization of alkenes bearing a hydroxy group using various types of organosilicon nucleophiles. Indium triiodide was the most effective catalyst, whereas typical Lewis acids such as TiCl4, AlCl3, and BF3·OEt2 were ineffective. Many functional groups were successfully introduced, and these resulted in yields of 31-86%. Various styrene derivatives were also applicable to this reaction. Mechanistic investigation revealed that the present hydrofunctionalization proceeded through Br?nsted acid-catalyzed intramolecular hydroalkoxylation of alkenes followed by InI3-catalyzed substitution reaction of cyclic ether intermediates.
