Selection
between Diastereomeric Kinetic vs Thermodynamic
Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate
and Difluoroacetaldehyde Ethyl Hemiacetal
Posted on 2018-07-18 - 20:18
Enantioselectivity increases with
increasing carbonyl electrophilicity
in 2-propanol-mediated reductive couplings of aldehydes with branched
aryl-substituted allylic acetates to form products of carbonyl anti-(α-aryl)allylation. This unusual phenomenon is
caused by aldehyde coordination to diastereomeric kinetic vs thermodynamic
carbonyl binding sites that deliver enantiomeric products. Exploiting
this effect, anti-diastereo- and enantioselective
(α-aryl)allylations of fluoral hydrate and difluoroacetaldehyde
ethyl hemiacetal were developed.
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Cabrera, James
M.; Tauber, Johannes; Zhang, Wandi; Xiang, Ming; Krische, Michael J. (2018). Selection
between Diastereomeric Kinetic vs Thermodynamic
Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzed anti-(α-Aryl)allylation of Aqueous Fluoral Hydrate
and Difluoroacetaldehyde Ethyl Hemiacetal. ACS Publications. Collection. https://doi.org/10.1021/jacs.8b05725
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AUTHORS (5)
JC
James
M. Cabrera
JT
Johannes Tauber
WZ
Wandi Zhang
MX
Ming Xiang
MK
Michael J. Krische
KEYWORDS
aryl-substituted allylic acetatesDiastereomeric Kinetic vs Thermodynamic Carbonyl Binding Modes Enables Enantioselective Iridium-Catalyzedenantiomeric productsDifluoroacetaldehyde Ethyl Hemiacetal Enantioselectivity increasescarbonyl electrophilicityaldehyde coordinationcarbonyl binding sitesform products2- propanol-mediated reductive couplingsfluoral hydratedifluoroacetaldehyde ethyl hemiacetalAqueous Fluoral Hydrate