TY - JOUR
T1 - Racemization and Deracemization through Intermolecular Redox Behaviour
AU - Engwerda, Anthonius H.J.
AU - Meekes, Hugo
AU - Bickelhaupt, F. Matthias
AU - Rutjes, Floris P.J.T.
AU - Vlieg, Elias
PY - 2019/7/22
Y1 - 2019/7/22
N2 - Chiral molecules exhibiting a quinone and/or hydroquinone moiety are ubiquitous in natural products and small molecule drugs. Herein, we describe a chiral quinone-hydroquinone molecule that racemizes through a reversible redox reaction. Using a combined computational and experimental approach, we show that this racemization proceeds via an intermolecular reaction mechanism. Starting from two achiral reactants, this molecule could be obtained in enantiopure form using Viedma ripening.
AB - Chiral molecules exhibiting a quinone and/or hydroquinone moiety are ubiquitous in natural products and small molecule drugs. Herein, we describe a chiral quinone-hydroquinone molecule that racemizes through a reversible redox reaction. Using a combined computational and experimental approach, we show that this racemization proceeds via an intermolecular reaction mechanism. Starting from two achiral reactants, this molecule could be obtained in enantiopure form using Viedma ripening.
KW - chiral resolution
KW - deracemization
KW - quinone
KW - racemization
KW - redox
UR - http://www.scopus.com/inward/record.url?scp=85068367741&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85068367741&partnerID=8YFLogxK
U2 - 10.1002/chem.201902438
DO - 10.1002/chem.201902438
M3 - Article
C2 - 31173419
AN - SCOPUS:85068367741
SN - 0947-6539
VL - 25
SP - 9639
EP - 9642
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
IS - 41
ER -
