300708-87-6Relevant academic research and scientific papers
Mechanistically Inspired Route toward Hexahydro-2H-chromenes via Consecutive [4 + 2] Cycloadditions
Ashtekar, Kumar Dilip,Ding, Xinliang,Toma, Edmond,Sheng, Wei,Gholami, Hadi,Rahn, Christopher,Reed, Paul,Borhan, Babak
, p. 3976 - 3979 (2016)
Utilizing two robust C-C bond-forming reactions, the Baylis-Hillman reaction and the Diels-Alder reaction, we report a highly enantio-, regio-, and diastereoselective synthesis of hexahydro-2H-chromenes via two sequential [4 + 2] cycloadditions. These tandem and formal cycloadditions have also been performed as a "one-pot" sequence to access the corresponding heterocycles constituting up to five contiguous stereocenters in excellent yields and stereoselectivity.
Stereoselective synthesis of cyclohexanones via phase transfer catalyzed double addition of nucleophiles to divinyl ketones
Silvanus, Andrew C.,Groombridge, Benjamin J.,Andrews, Benjamin I.,Kociok-Koehn, Gabriele,Carbery, David R.
supporting information; experimental part, p. 7491 - 7493 (2010/12/30)
Functionalized cyclohexanones are formed in excellent yield and diastereoselectivity from a phase transfer catalyzed double addition of active methylene pronucleophiles to nonsymmetrical divinyl ketones.
A Synthetic and Computational Investigation into the Direct Synthesis of α -Hydroxymethylated Enones from β-keto Phosphonates
Ryan, Sarah J.,Thompson, Christopher D.,Lupton, David W.
experimental part, p. 720 - 727 (2010/02/16)
The synthesis of a range of -hydroxymethylated enones has been achieved using the Villiras modification of the HornerWadsworthEmmons (HWE) reaction. Scope, limitations, and mechanistic aspects of this reaction were investigated using a combination of synthetic and computational studies. These investigations support a SchlosserCorey type reaction mechanism that is balanced between two pathways with the outcome influenced by the steric environment of the substrate. CSIRO 2009.
A general procedure for the preparation of β-ketophosphonates
Maloney, Kevin M.,Chung, John Y. L.
supporting information; experimental part, p. 7574 - 7576 (2009/12/28)
(Chemical Equation Presented) A mild, high-yielding procedure for the preparation of β-ketophosphonates is described. The condensation is general with respect to the ester and phosphonate, and the products are obtained in high yields within minutes at 0°C. The reaction procedure is operationally simple and amenable to large-scale preparations. 2009 American Chemical Society.
Zinc-Mediated Chain Extension of β-Keto Phosphonates
Verbicky, Christopher A.,Zercher, Charles K.
, p. 5615 - 5622 (2007/10/03)
A variety of β-keto phosphonates can be converted to γ-keto phosphonates through reaction with ethyl(iodomethyl)zinc. The presence of α-alkyl substituents, Lewis basic functionality, and modestly acidic NH-protons are accommodated in substrates of this reaction. Chain extension of β-keto phosphonates that contained olefinic functionality proceeded more quickly than cyclopropanation; however, it was not possible to effect the chain extension to the exclusion of cyclopropane formation. A primary reason for this imperfect chemoselectivity appears to be the slow chain extension of β-keto phosphonates. Nevertheless, the simplicity, the scope, and efficiency of this method serve to make it an attractive alternative to the established methods for γ-keto phosphonate formation.
Synthesis of functionalized phenolic derivatives via the benzannulation of dienylketenes formed by a thermal Wolff rearrangement of α-diazo-β-keto compounds
Collomb, Didier,Deshayes, Christian,Doutheau, Alain
, p. 6665 - 6684 (2007/10/03)
Eleven conjugated dienyl α-diazo-β-keto derivatives were prepared from α,β-unsaturated carbonyl compounds. Their thermolysis induced a Wolff rearrangement generating an intermediate dienyl ketene whose isomer which has the required configuration of the internal double bond underwent a benzannylation thus forming the corresponding phenolic derivatives. When γ-substituted by a methoxy group both stereoisomers of the diazo compounds gave rise to the phenolic derivatives due to the reversible formation of an intermediate cyclobutenone which permitted the isomerization of the nonproductive transient dienylketene into the productive one.
