116797-34-3Relevant academic research and scientific papers
Stereoselective selenium catalyzed dihydroxylation and hydroxymethoxylation of alkenes
Santi, Claudio,Di Lorenzo, Rosalia,Tidei, Caterina,Bagnoli, Luana,Wirth, Thomas
, p. 10530 - 10535,6 (2012)
The selenium atom of the selenocysteine plays a crucial role in the reduction of peroxides. Herein we showed that, in the absence of a thiol cofactor, the same aminoacid efficiently catalyzed the dihydroxylation of carbon-carbon double bonds leading to the stereoselective formation of 1,2-diols at room temperature and in on water conditions. Alternatively, in the presence of methanol, the corresponding β-methoxyalcohol can be prepared. The stereoselectivity of the reaction will be discussed and NMR evidences of the actual catalyst are here reported.
Hydrodealkenylative C(sp3)–C(sp2) bond fragmentation
Smaligo, Andrew J.,Swain, Manisha,Quintana, Jason C.,Tan, Mikayla F.,Kim, Danielle A.,Kwon, Ohyun
, p. 681 - 685 (2019/06/11)
Chemical synthesis typically relies on reactions that generate complexity through elaboration of simple starting materials. Less common are deconstructive strategies toward complexity—particularly those involving carbon-carbon bond scission. Here, we introduce one such transformation: the hydrodealkenylative cleavage of C(sp3)–C(sp2) bonds, conducted below room temperature, using ozone, an iron salt, and a hydrogen atom donor. These reactions are performed in nonanhydrous solvents and open to the air; reach completion within 30 minutes; and deliver their products in high yields, even on decagram scales. We have used this broadly functionality tolerant transformation to produce desirable synthetic intermediates, many of which are optically active, from abundantly available terpenes and terpenoid-derived precursors. We have also applied it in the formal total syntheses of complex molecules.
