Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 3, Pages 766-770Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201308268
Keywords
desymmetrization; meso compounds; organocatalysis; quaternary centers; tetrahydropyranes
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Funding
- Aix-Marseille University
- CNRS
- Conseil General des Bouches du Rhone
- COST ORCA Action [0905]
- ANR (Agence Nationale de la Recherche) [ANR-10-JCJC-0710]
- Agence Nationale de la Recherche (ANR) [ANR-10-JCJC-0710] Funding Source: Agence Nationale de la Recherche (ANR)
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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.
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