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Direct Carbon-Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters

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Date
2010
Authors
Kohler, Mark C
Yost, Julianne M
Garnsey, Michelle R
Coltart, Don M
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Abstract
An asymmetric Mannich reaction of phenylacetate thioesters and sulfonylimines using cinchona alkaloid-based amino (thio)urea catalysts is reported that employs proximity-assisted soft enolization. This approach to enolization is based on the cooperative action of a carbonyl-activating hydrogen bonding (thio)urea moiety and an amine base contained within a single catalytic entity to facilitate intracomplex deprotonation. Significantly, this allows thioesters over a range of acidity to react efficiently, thereby opening the door to the development of a general mode of enolization-based organocatalysis of monocarboxylic acid derivatives.
Type
Other article
Subject
baylis-hillman reaction
direct aldol addition
citrate synthase
michael reaction
bifunctional organocatalysts
trifluoroethyl
thioesters
intramolecular reactions
polyketide synthases
group
participation
half-thioesters
chemistry, organic
Permalink
https://hdl.handle.net/10161/4107
Published Version (Please cite this version)
10.1021/ol101152b
Citation
Kohler,Mark C.;Yost,Julianne M.;Garnsey,Michelle R.;Coltart,Don M.. 2010. Direct Carbon-Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters. Organic letters 12(15): 3376-3379.
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