Direct Carbon-Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters
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 articleSubject
baylis-hillman reactiondirect 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/10161/4107Published Version (Please cite this version)
10.1021/ol101152bCitation
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.
Collections
More Info
Show full item record
Articles written by Duke faculty are made available through the campus open access policy. For more information see: Duke Open Access Policy
Rights for Collection: Scholarly Articles
Works are deposited here by their authors, and represent their research and opinions, not that of Duke University. Some materials and descriptions may include offensive content. More info