Browsing by Author "Coltart, Don M"
Now showing items 1-5 of 5
-
Development of a Strategy for the Asymmetric Synthesis of Polycyclic Polyprenylated Acylphloroglucinols via N-Amino Cyclic Carbamate Hydrazones: Application to the Total Synthesis of (+)-Clusianone
(2010)A broadly applicable asymmetric synthetic strategy utilizing N-amino cyclic carbamate alkylation that provides access to the various stereochemical permutations of a common structural motif found in many polycyclic polyprenylated ... -
Direct Carbon-Carbon Bond Formation via Reductive Soft Enolization: A Kinetically Controlled syn-Aldol Addition of alpha-Halo Thioesters and Enolizable Aldehydes
(2010)The direct addition of enolizable aldehydes and a-halo thioesters to produce beta-hydroxy thioesters enabled by reductive soft enolization is reported. The transformation is operationally simple and efficient and has the ... -
Direct Carbon-Carbon Bond Formation via Soft Enolization: A Biomimetic Asymmetric Mannich Reaction of Phenylacetate Thioesters
(2010)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 ... -
Direct carbon-carbon bond formation via soft enolization: aldol addition of alpha-halogenated thioesters
(2011)alpha-Halo thioesters undergo soft enolization and syn-selective direct aldol addition to aldehydes in the presence of MgBr2 center dot OEt2 and i-Pr2NEt to produce alpha-halo-beta-hydroxy thioesters. -
Origins of Stereoselectivity in the alpha-Alkylation of Chiral Hydrazones
(2010)Density functional theory calculations and experiment reveal the origin of stereoselectivity in the deprotonation-alkylation of chiral N-amino cyclic carbamate (ACC) hydrazones. When the ACC is a rigid, camphor-derived carbamate, ...
