Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 50, Pages 16052-16056Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201709844
Keywords
diols; enantioselectivity; kinetic resolution; natural products; organocatalysis
Categories
Funding
- Aix Marseille Universite (AMU)
- CNRS
- COST ORCA Action [0905]
- French Research Ministry
- 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)
Ask authors/readers for more resources
The concept of a synergistic double catalytic kinetic resolution (DoCKR) as described in this article was successfully applied to racemic acyclic anti-1,3-diols, a common motif in natural products. This process takes advantage of an additive Horeau amplification involving two successive enantioselective organocatalytic acylation reactions, and leads to diesters and recovered diols with high enantiopurities. It was first developed with C-2-symmetrical diols and then further extended to non-C-2-symmetrical anti diols to prepare useful chiral building blocks. The protocol is highly practical as it only requires 1mol% of a commercially available organocatalyst and leads to easily separable products. This procedure was applied to the shortest reported total synthesis of (+)-cryptocaryalactone, a natural product with anti-germinative activity.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available