1192756-82-3Relevant academic research and scientific papers
Stereocontrol of all-carbon quaternary centers through enantioselective desymmetrization of meso primary diols by organocatalyzed acyl transfer
Roux, Christèle,Candy, Mathieu,Pons, Jean-Marc,Chuzel, Olivier,Bressy, Cyril
, p. 766 - 770 (2014/01/23)
The symmetry breaking of meso primary diols bearing a tetrahydropyran ring was employed, using catalytic asymmetric acyl transfer, to control all-carbon quaternary stereocenters. The planar chiral Fu DMAP catalyst was used in this reaction to reach a high degree of enantioselectivity (up to 97:3 e.r.) through a synergic effect combining a desymmetrization step and a kinetic resolution. Moreover, a beneficial effect was exhibited by C6F6 solvent, yielding the first example of an organocatalyzed asymmetric acyl transfer. The desymmetrized monoesters were then used to obtain, after a straightforward ring opening sequence, complex polyketide building blocks bearing all-carbon quaternary stereocenters. Smashing the mirror: The symmetry breaking of meso primary diols was employed to control all-carbon quaternary stereocenters using catalytic asymmetric acyl transfer. The planar chiral Fu DMAP catalyst was used to reach a high degree of enantioselectivity (up to 97:3 e.r.) through a synergic effect, combining a desymmetrization step and a kinetic resolution. Copyright
Enantioselective enzymatic desymmetrization of highly functionalized meso tetrahydropyranyl diols
Candy, Mathieu,Audran, Gerard,Bienayme, Hugues,Bressy, Cyril,Pons, Jean-Marc
supporting information; experimental part, p. 4950 - 4953 (2010/01/16)
The enantioselective enzymatic desymmetrization of several highly substituted meso-tetrahydropyranyl diols is described. This transformation leads to valuable building blocks containing up to five stereogenic centers, which are revealed in a single step w
