17040-65-2Relevant articles and documents
Synthetic Exploration Involving Nickel Acylate Complexes and Electrophilic Alkenes
Hermanson, James R.,Gunther, Michael L.,Belletire, John L.,Pinhas, Allan R.
, p. 1900 - 1903 (1995)
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Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Models Cannot Be Used
Bartolo, Nicole D.,Demkiw, Krystyna M.,Valentín, Elizabeth M.,Hu, Chunhua T.,Arabi, Alya A.,Woerpel
, p. 7203 - 7217 (2021/05/29)
The stereoselectivities of reactions of allylmagnesium reagents with chiral ketones cannot be easily explained by stereochemical models. Competition experiments indicate that the complexation step is not reversible, so nucleophiles cannot access the widest range of possible encounter complexes and therefore cannot be analyzed easily using available models. Nevertheless, additions of allylmagnesium reagents to a ketone can still be stereoselective provided that the carbonyl group adopts a conformation that leads to one face being completely blocked from the approach of the allylmagnesium reagent.
Pd-catalyzed synthesis of α,β-unsaturated ketones by carbonylation of vinyl triflates and nonaflates
Zhang, Shaoke,Neumann, Helfried,Beller, Matthias
supporting information, p. 5938 - 5941 (2019/05/27)
A general and highly chemoselective Pd-catalyzed protocol for the synthesis of α,β-unsaturated ketones by carbonylation of vinyl triflates and nonaflates is presented. Applying the specific monophosphine ligand cataCXium A, the synthesis of various vinyl ketones as well as carbonylated natural product derivatives proceeds in good yields.
Products of reaction of 1-phenyltricyclo[4.1.0.02,7]heptane with N-iodosuccinimide in aqueous THF
Vasin,Romanova,Razin
, p. 1749 - 1752 (2017/12/29)
Iodohydroxylation of 1-phenyltricyclo[4.1.0.02,7]heptane in aqueous THF at 20°C with N-iodosuccinimide proceeds at the central bicyclobutane bond C1–C7 and results in the formation of two-component mixture of diastereomeric 7-iodo-6-phenyl-6-norpinanols in the ratio 1 : 1.8 in favor of the product of the anti-addition. Treating of iodonorpinanols with trimethylamine in aqueous THF affords 1-benzoylcyclohex-1-ene as a result of 1,4-dehydroiodination accompanied with the Grob fragmentation of the carbon scaffold.
