71434-19-0Relevant academic research and scientific papers
Stereoselective synthesis of substituted oxocene cores by Lewis acid promoted cyclization
Ghosh, Arun K.,Tomaine, Anthony J.,Cantwell, Kelsey E.
, p. 396 - 399 (2016)
Substituted oxocene derivatives have been synthesized by Lewis acid catalyzed reactions of ε-hydroxyalkene and substituted aromatic aldehydes. The Cu(OTf)2-bis-phosphine catalyzed reaction typically provides substituted dihydropyran derivatives through an olefin migration followed by a Prins cyclization. The corresponding reaction catalyzed by TMSOTf or BF3·OEt2 provided eight-membered cyclic ethers (oxocenes), selectively. This methodology provides convenient access to a variety of 2,4,8-trisubstituted oxocenes in good yields and excellent diastereoselectivities.
Cu(II)-Catalyzed Olefin Migration and Prins Cyclization: Highly Diastereoselective Synthesis of Substituted Tetrahydropyrans
Ghosh, Arun K.,Nicponski, Daniel R.
, p. 4328 - 4331 (2011/10/05)
Metal-ligand complexes of Cu(OTf)2 with an appropriate bisphosphine ligand have been shown to effectively catalyze the formation of substituted tetrahydropyrans via a sequential olefin migration and Prins-type cyclization. This methodology provides convenient access to a variety of functionalized tetrahydropyrans in excellent diastereoselectivities and good to excellent yields.
