Efficient, scalable asymmetric synthesis of an epoxy quinol via Noyori desymmetrization of a meso diketone
by Clay, David R.; Rosenberg, Ashley G.; McIntosh, Matthias C.
Epoxy quinol la was prepared on a multi-gram scale by Noyori transfer hydrogenative desymmetrization of the readily available meso-epoxy diketone 4. Although the intrinsic enantioselectivity for the desymmetrization was modest (82:18 er at 4% conversion), a highly enantiopure product (99.6:0.4 er) could be obtained in one operation in 44% yield via kinetic resolution of the minor enantiomer with long reaction times (48 h), or in 73% yield by combination with an enzymatic resolution of a 93:7 er mixture.
- Journal
- Tetrahedron-Asymmetry
- Volume
- 22
- Issue
- 7
- Year
- 2011
- Start Page
- 713-716
- URL
- https://dx.doi.org/10.1016/j.tetasy.2011.04.022
- ISBN/ISSN
- 1362-511X; 0957-4166
- DOI
- 10.1016/j.tetasy.2011.04.022