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Double Catalytic Kinetic Resolution (DoCKR) of Acyclic anti ‐1,3‐Diols: The Additive Horeau Amplification
Author(s) -
Merad Jérémy,
Borkar Prashant,
Caijo Frédéric,
Pons JeanMarc,
Parrain JeanLuc,
Chuzel Olivier,
Bressy Cyril
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201709844
Subject(s) - kinetic resolution , acylation , chemistry , enantioselective synthesis , catalysis , natural product , separable space , organic chemistry , diol , combinatorial chemistry , stereochemistry , mathematics , mathematical analysis
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 1 mol % 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.