24731-17-7Relevant articles and documents
Synthesis of γ-Haloesters and γ-Ketoesters by Homolytic Addition of Carbon Radicals Generated by α-Haloesters and Triethylborane to Alkenes and Silyl Enol Ethers
Baciocchi, Enrico,Muraglia, Ester
, p. 2763 - 2766 (1994)
An efficient synthesis of γ-haloesters has been achieved, under very mild conditions, by addition of electrophilic carbon radicals CH(R)CO2Et (R=H, Me, CO2Et) generated by XCH(R)CO2Et (X=Br, I)/BEt3/air in DMSO to alkenes and cycloalkenes.The synthesis of γ-ketoesters is also possible when silyl enol ethers are used as the substrates.
Photocontrolled Cobalt Catalysis for Selective Hydroboration of α,β-Unsaturated Ketones
Beltran, Frédéric,Bergamaschi, Enrico,Funes-Ardoiz, Ignacio,Teskey, Christopher J.
, p. 21176 - 21182 (2020/09/17)
Selectivity between 1,2 and 1,4 addition of a nucleophile to an α,β-unsaturated carbonyl compound has classically been modified by the addition of stoichiometric additives to the substrate or reagent to increase their “hard” or “soft” character. Here, we demonstrate a conceptually distinct approach that instead relies on controlling the coordination sphere of a catalyst with visible light. In this way, we bias the reaction down two divergent pathways, giving contrasting products in the catalytic hydroboration of α,β-unsaturated ketones. This includes direct access to previously elusive cyclic enolborates, via 1,4-selective hydroboration, providing a straightforward and stereoselective route to rare syn-aldol products in one-pot. DFT calculations and mechanistic experiments confirm two different mechanisms are operative, underpinning this unusual photocontrolled selectivity switch.
First and Highly Stereoselective Synthesis of Both Enantiomers of Octahydroindole-2-phosphonic Acid (OicP)
Viveros-Ceballos, José Luis,Martínez-Toto, Erick Iván,Eustaquio-Armenta, César,Cativiela, Carlos,Ordó?ez, Mario
, p. 6781 - 6787 (2017/12/07)
We report the first stereoselective synthesis of (2R,3aR,7aR)- and (2S,3aS,7aS)-octahydroindole-2-phosphonic acid 2 (OicP derivatives). The key points are the highly diastereoselective synthesis of cis-fused bicyclic (3aR,7aR)- and (3aS,7aS)-pyrrolidin-2-ones 4 through a dynamic kinetic resolution of racemic γ-keto acid (±)-5 with (R)- and (S)-phenylglycinol via Meyers' bicyclic lactams, and the highly diastereoselective addition of trimethyl phosphite to the N-acyliminium ions 3 obtained from 4.
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Page/Page column 52, (2015/12/17)
Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.