1207948-68-2Relevant academic research and scientific papers
Tandem Transformations via Friedel-Crafts Acylation Followed by a Ring-Expansion, Ring-Opening, and Cycloisomerization Sequence
Kim, Hun Young,Oh, Kyungsoo
, p. 696 - 699 (2019/01/30)
A tandem synthetic route to a diverse array of cyclic compounds has been developed from Friedel-Crafts acylation of alkynes followed by the microwave irradiation of β-chlorovinyl ketone intermediates. The stereoisomeric β-chlorovinyl ketone intermediates smoothly underwent a thermal α-vinyl enolization and ring expansion to vinyl and carbocyclic furans as well as cyclopetene derivatives in good to excellent yields without the need for any catalysts.
Studies on elimination pathways of β-halovinyl ketones leading to allenyl and propargyl ketones and furans under the action of mild bases
Kim, Hun Young,Li, Jian-Yuan,Oh, Kyungsoo
, p. 11132 - 11145 (2013/02/23)
The elimination pathway of stereochemically defined β-halovinyl ketones has been investigated using a mild base, NEt3, leading to the formation of allenyl ketones and propargyl ketones. A preferential α-vinyl enolization of (E)-β-chlorovinyl ke
Stereoselective ring expansion of vinyl oxiranes: Mechanistic insights and natural product total synthesis
Brichacek, Matthew,Batory, Lindsay A.,Njardarson, Jon T.
supporting information; experimental part, p. 1648 - 1651 (2010/06/15)
"Chemical Equation Presented" What a (strain) relief! The first broadly applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac = hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ring-expansion reaction has been employed in the asymmetric total synthesis of (+)-goniothalesdiol.
Gold catalysis: Efficient 1,3-induction with diastereotopic homopropargyl alcohols in the phenol synthesis
Hashmi, A. Stephen K.,Hamzic, Melissa,Rudolph, Matthias,Ackermann, Martin,Rominger, Frank
experimental part, p. 2469 - 2481 (2010/03/25)
Furans with diastereotopic alkynyl groups were prepared and then converted to anellated phenols in gold-catalyzed reactions. In all cases a highly diastereoselective reaction was observed. The stereochemical outcome of the 1,3-induction could be assigned
Gold catalysis: Enantiotopos selection
Hashmi, A. Stephen K.,Hamzie, Melissa,Rominger, Frank,Bats, Jan W.
supporting information; experimental part, p. 13318-13322+13274 (2010/06/17)
"Chemical Equation Presented" Selecting one out of two enantiotopic alkynes: A furan-diyne substrate with enantiotopic alkynyl groups was prepared and the gold-catalyzed cyclo isomerization by a series of different chiral cationic gold(I) complexes was in
