929903-74-2Relevant academic research and scientific papers
Enantioselective rhodium-catalyzed hydroacylation to access the four stereoisomers of anti-rodent difenacoum
Jacolot, Ma?wenn,Moebs-Sanchez, Sylvie,Popowycz, Florence
, p. 1636 - 1639 (2017/04/04)
An efficient asymmetric synthesis of the four stereoisomers of difenacoum, an anticoagulant currently used as a rodenticide in racemic form, is performed using a key step of rhodium catalyzed enantioselective intramolecular hydroacylation. Optimization of the last step, condensation of 4-hydroxycoumarin with chiral 3-([1,1′-biphenyl]-4-yl)-1,2,3,4-tetrahydronaphthalen-1-ol, is also discussed. After chromatographic separation of the cis and trans diastereoisomers, the four stereoisomers were all obtained with excellent enantioselective and diastereoselective excess (ee?≈?96% and de >96%).
Enantioselective Intramolecular Hydroacylation of Unactivated Alkenes: An NHC-Catalyzed Robust and Versatile Formation of Cyclic Chiral Ketones
Janssen-Müller, Daniel,Schedler, Michael,Fleige, Mirco,Daniliuc, Constantin G.,Glorius, Frank
, p. 12492 - 12496 (2015/10/12)
A highly enantioselective intramolecular N-heterocyclic carbene (NHC)-catalyzed hydroacylation reaction gives access to a range of cyclic ketones from unactivated olefin-substituted aldehydes (up to 99% ee). Remarkably, aliphatic aldehydes were also transformed efficiently in an NHC-catalyzed hydroacylation reaction for the first time. 100% Organic: A highly enantioselective N-heterocyclic carbene (NHC)-catalyzed intramolecular hydroacylation of aromatic and, more interestingly, aliphatic aldehydes with unactivated olefins offers access to a range of cyclic α-chiral ketones bearing quaternary centers. The reaction was found to be highly robust and proceeds with excellent yield in the presence of a diverse range of functional groups.
Model studies for the synthesis of the antibiotic lactonamycin and the discovery of new reactions and mechanisms for the construction of substituted heterocycles
Parsons, Philip J.,Board, Jonathan,Faggiani, Davide,Hitchcock, Peter B.,Preece, Lewis,Waters, Alexander J.
experimental part, p. 6526 - 6533 (2010/10/19)
A new and highly efficient route for the construction of a model for the synthesis of lactonamycin 1 is reported. The chemistry has been utilised for the synthesis of heterocyclic rings, and new reactions for the synthesis of dienes and alkynes are report
A novel cyclisation strategy for the synthesis of lactonamycin: A new route to highly functionalised heterocyclic rings
Parsons, Philip J.,Board, Johnathan,Waters, Alexander J.,Hitchcock, Peter B.,Wakenhut, Florian,Walter, Daryl S.
, p. 3243 - 3246 (2008/09/17)
A novel thermal cascade reaction equivalent to the well-known [2+2+2] cycloaddition has been developed which is clean and reliable and does not involve the use of metal ions. This highly efficient method has been used to construct a model for the synthesi
