40648-09-7Relevant academic research and scientific papers
Catalytic formal homo-Nazarov cyclization
De Simone, Filippo,Andres, Julien,Torosantucci, Riccardo,Waser, Jerome
supporting information; experimental part, p. 1023 - 1026 (2009/07/18)
The first catalytic method for the cyclization of vinyl-cyclopropyl ketones (formal homo-Nazarov reaction) is reported. Starting from activated cyclopropanes, heterocyclic, and carbocyclic compounds were obtained under mild conditions using Bronsted acid catalysts. Preliminary investigation of the reaction mechanism indicated a stepwise process.
Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides
Shirakawa, Eiji,Imazaki, Yusuke,Hayashi, Tamio
supporting information; experimental part, p. 5088 - 5090 (2009/12/08)
In the presence of a ruthenium catalyst, alkenyl triflates were found to be transformed to the corresponding bromides, chlorides and iodides simply by treatment with a lithium halide (1.2 equiv.). The Royal Society of Chemistry 2009.
Stereoselective benzannulations and cyclohexadienone annulations of Fischer carbene complexes in the synthesis of decala-2,4-dien-1-ones and in the synthesis of tetralin chromium tricarbonyl complexes
Hsung, Richard P.,Wulff, William D.,Challener, Cynthia A.
, p. 773 - 789 (2007/10/03)
The first general study is reported on the stereoselectivity of the benzannulation reaction involving diastereoselection at the planar center of chirality of the newly formed arene ring complexed to chromium that is induced from a chiral carbon center on the carbene complex. The stereochemistry of a number of 5- and 8-substituted tetralin chromium tricarbonyl complexes, which are produced from the benzannulations of cyclohexenyl carbene complexes with chiral centers at the 3- and 6-positions, is determined. These results are compared with the stereochemistry of the formation of 5,9- and 8,9-disubstituted decala-2,4-dien-1-ones produced from the reactions of the same carbene complexes bearing an additional substituent in the 2-position of the cyclohexenyl ring. The benzannulation reaction is most selective with 3-substituted cyclohexenyl carbene complexes giving predominately the anti-isomer of the 8-substituted tetralin chromium tricarbonyl complexes. In contrast, the cyclohexadienone annulation is most selective with 6-substituted cyclohexenyl carbene complexes giving predominately the trans-isomer of the 5,9-disubstituted decala-2,4-dien-1-ones. A mechanistic accounting of the stereochemical results is proposed which is predicated on three assumptions: 1) that the η1,η3-vinyl carbene complexed intermediate is in equilibrium, 2) vinyl ketene complex formation is irreversible and occurs with a carbon monoxide migration that is in concert with coordination of the double bond of the cyclohexene ring, and 3) the electrocyclic ring closure of the vinyl ketene complex is stereospecific.
A Regioselective Entry to Vinyllithiums from Unsymmetrical Ketones via Enol Triflates
Wulff, William D.,Peterson, Glen A.,Bauta, William E.,Chan, Kin-Shing,Faron, Katherine L.,et al.
, p. 277 - 279 (2007/10/02)
The first method for the regioselective preparation of either the "kinetic" or "thermodynamic" vinyllithium from an unsymmetrical ketone is described
