78349-04-9Relevant academic research and scientific papers
Photocatalytic Reductive Radical-Polar Crossover for a Base-Free Corey–Seebach Reaction
Crespi, Stefano,Donabauer, Karsten,K?nig, Burkhard,Murugesan, Kathiravan,Rozman, Ur?a
supporting information, p. 12945 - 12950 (2020/09/23)
A metal-free generation of carbanion nucleophiles is of prime importance in organic synthesis. Herein we report a photocatalytic approach to the Corey–Seebach reaction. The presented method operates under mild redox-neutral and base-free conditions giving the desired product with high functional group tolerance. The reaction is enabled by the combination of photo- and hydrogen atom transfer (HAT) catalysis. This catalytic merger allows a C?H to carbanion activation by the abstraction of a hydrogen atom followed by radical reduction. The generated nucleophilic intermediate is then capable of adding to carbonyl electrophiles. The obtained dithiane can be easily converted to the valuable α-hydroxy carbonyl in a subsequent step. The proposed reaction mechanism is supported by emission quenching, radical–radical homocoupling and deuterium labeling studies as well as by calculated redox-potentials and bond strengths.
Analogues of Acifran: Agonists of the high and low affinity niacin receptors, GPR109a and GPR109b
Jung, Jae-Kyu,Johnson, Benjamin R.,Duong, Tracy,Decaire, Marc,Uy, Jane,Gharbaoui, Tawfik,Boatman, P. Douglas,Sage, Carleton R.,Chen, Ruoping,Richman, Jeremy G.,Connolly, Daniel T.,Semple, Graeme
, p. 1445 - 1448 (2007/10/03)
Recently identified GPCRs, GPR109a and GPR109b, the high and low affinity receptors for niacin, may represent good targets for the development of HDL elevating drugs for the treatment of atherosclerosis. Acifran, an agonist of both receptors, has been tested in human subjects, yet until recently very few analogs had been reported. We describe a series of acifran analogs prepared using newly developed synthetic pathways and evaluated as agonists for GPR109a and GPR109b, resulting in identification of compounds with improved activity at these receptors.
Selectivities in the Reactions of Alkyl-, Aryl- and Heterosubstituted Organotitanium Compounds
Weidmann, Beat,Widler, Leo,Olivero, Alan G.,Maycock, Christopher D.,Seebach, Dieter
, p. 357 - 361 (2007/10/02)
Solutions of the title compounds R-Ti(OR')3 (1) are generally available from organolithium (or magnesium) derivatives according to equation 1.It is shown (table 1) that some heterosubstituted organotitanium compounds are more stable thermally than their lithium counterparts.The reagents 1 are highly selective carbonylophiles (Tables 1 and 2), their reactivity can be modified by variation of the R'O-group (Table 3) and with the chiral (S)-2-methyl-1-butoxy group an enantioselective addition can be achieved.
