Journal ArticleDOI
Highly Enantioselective Construction of a Quaternary Carbon Center of Dihydroquinazoline by Asymmetric Mannich Reaction and Chiral Recognition
TLDR
In this paper, a chiral trifluoromethyl quaternary carbon center of dihydroquinazoline was constructed by an asymmetric Mannich reaction and chiral recognition.Abstract:
The highly enantioselective construction of a quaternary carbon center of dihydroquinazoline by an asymmetric Mannich reaction and chiral recognition are described The key transformation was to establish the chiral trifluoromethyl quaternary carbon center by a diamine-Bronsted acid-catalyzed enantioselective and regioselective Mannich reaction of a methyl ketone and 4-trifluoromethyldihydroquinazoline An unusual phenomenon of self-discrimination of enantiomers in hydrogen-bonded dimers was observed A valuable intermediate was transformed into the enantiopure HIV reverse transcriptase inhibitor DPC 083 (>999 ee) simply by reduction of the carbonyl group and elimination of the hydroxy group in hexamethylphosphoric tramide (HMPA)read more
Citations
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Journal ArticleDOI
Asymmetric construction of stereogenic carbon centers featuring a trifluoromethyl group from prochiral trifluoromethylated substrates.
TL;DR: This poster presents a probabilistic analysis of the response of Na6(CO3)(SO4)(SO3) to Na2SO4 using a high-resolution X-ray diffraction analysis for the stationary phase.
Journal ArticleDOI
Catalytic Enantioselective Formation of C−C Bonds by Addition to Imines and Hydrazones: A Ten-Year Update
Journal ArticleDOI
Enantioselective Synthesis of AG‐041R by using N‐Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts
TL;DR: X-ray crystallographic analysis revealed that the hydrogen bonding between the sulfonimide proton and the 8-quinolyl nitrogen atom plays an important role in exerting the enantioselectivity of the reaction.
Journal ArticleDOI
Asymmetric organocatalysis: an enabling technology for medicinal chemistry
TL;DR: A comprehensive overview of the applications of asymmetric organocatalysis in medicinal chemistry can be found in this article, with a focus on the preparation of antiviral, anticancer, neuroprotective, cardiovascular, antibacterial, and antiparasitic agents, as well as several miscellaneous bioactive agents.
Journal ArticleDOI
Hydrogen-Bond-Directed Enantioselective Decarboxylative Mannich Reaction of β-Ketoacids with Ketimines: Application to the Synthesis of Anti-HIV Drug DPC 083
TL;DR: Efforts are reported in developing a hydrogenbond-directed enantioselective decarboxylative Mannich reaction of b-ketoacids by employing cyclic N-acyl ketimines as the electrophilic acceptor and this new reaction was cooperatively promoted by saccharide-based bifunctional organocatalysts.
References
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Journal ArticleDOI
Highly enantioselective construction of a chiral tertiary carbon center by alkynylation of a cyclic N-acyl ketimine: an efficient preparation of HIV therapeutics.
Biao Jiang,Yu-Gui Si +1 more
Journal ArticleDOI
3-Pyrrolidinecarboxylic acid for direct catalytic asymmetric anti-Mannich-type reactions of unmodified ketones.
TL;DR: The position of the carboxylic acid group on the pyrrolidine ring directs the stereoselection of the catalyzed reaction, providing either syn- or anti-Mannich products.
Journal ArticleDOI
The Importance of Iminium Geometry Control in Enamine Catalysis: Identification of a New Catalyst Architecture for Aldehyde–Aldehyde Couplings
TL;DR: This work has advanced the proline-catalysis concept to the first example of a direct enantioselective cross-coupling of aldehyde substrates (Scheme 1), a powerful yet elusive aldol variant that had previously only been carried out within the realm of enzymatic catalysis.
Journal ArticleDOI
Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: importance of the 3-acid group on pyrrolidine for stereocontrol.
Haile Zhang,Susumu Mitsumori,Naoto Utsumi,Masanori Imai,Noemi Garcia-Delgado,Maria Mifsud,Klaus Albertshofer,Paul Ha-Yeon Cheong,Kendall N. Houk,Fujie Tanaka,Carlos F. Barbas +10 more
TL;DR: Evaluation of a series of pyrrolidine-based catalysts indicated that the acid group at the beta-position of the p Pyrrolidine ring of the catalyst played an important role in forwarding the carbon-carbon bond formation and in directing anti-selectivity and enantioselectivity.
Journal ArticleDOI
The Scope of the Direct Proline-Catalyzed Asymmetric Addition of Ketones to Imines
Wolfgang Notz,Shin-ichi Watanabe,Naidu S. Chowdari,Guofu Zhong,Juan M. Betancort,Fujie Tanaka,Carlos F. Barbas +6 more
TL;DR: The methodology developed was applied as a powerful approach toward the synthesis of enantiomerically pure functionalized α-amino acids, γ-lactones, oxime-functionalized amino acids as well as pharmacologically important targets such as (R)-cyclohexylglycine.