144270-76-8Relevant articles and documents
Stereoselective alkenylation of activated olefins via nickel-catalyzed electroreductive coupling
Condon-Gueugnot, Sylvie,Dupre, Daniel,Nedelec, Jean-Yves,Perichon, Jacques
, p. 1457 - 1460 (1997)
The nickel-catalyzed electroreductive conjugate addition of (Z)- or (E)-alkyl halides to electron-deficient olefins in the presence of a sacrificial iron rod as the anode proceeds with complete retention of the stereochemistry of the alkenyl part and affo
Palladium-Catalyzed Regioselective C-H Iodination of Unactivated Alkenes
Schreib, Benedikt S.,Carreira, Erick M.
supporting information, p. 8758 - 8763 (2019/06/13)
A palladium-catalyzed C-H iodination of unactivated alkenes is reported. A picolinamide directing group enables the regioselective functionalization of a wide array of olefins to furnish iodination products as single stereoisomers. Mechanistic investigations suggest the reversible formation of a six-membered alkenyl palladacycle intermediate through a turnover-limiting C-H activation.
One-pot regio- and stereoselective cyclization of 1,2,n-triols
Zheng, Tao,Narayan, Radha S.,Schomaker, Jennifer M.,Borhan, Babak
, p. 6946 - 6947 (2007/10/03)
A simple and efficient process to cyclize triols containing a 1,2-diol functionality with a pendant hydroxyl group is presented. The one-pot procedure converts the 1,2-diol into an ortho ester in situ, which upon treatment with a Lewis acid generates a cyclic acetoxonium intermediate. This intermediate is subsequently trapped by the pendant hydroxyl group to generate a cyclic ether. The stereochemistry of the 1,2-diol is transferred to the product with complete fidelity (inversion at the site of cyclization), and the reaction proceeds with high regioselectivity. The process is akin to the Lewis acid-catalyzed intramolecular ring-opening of epoxides with hydroxyl groups yielding cyclic ethers of various sizes with regio- and stereochemical control. Copyright
