- N-Heterocyclic Carbene-Catalyzed Synthesis of α-Trifluoromethyl Esters
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The N-heterocyclic carbene (NHC)-catalyzed trifluoromethylation of α-chloro aldehydes was developed, allowing straightforward access to valuable α-trifluoromethyl ester derivatives. The unique combination of an electrophilic trifluoromethylation reagent with NHC catalysis was the key for the functionalization of a broad range of α-chloro aldehydes, and the products are formed in moderate to good yields. Investigations of the enantioselective version of this reaction afforded the enantioenriched products in moderate yields with good ee values.
- Gelat, Fabien,Patra, Atanu,Pannecoucke, Xavier,Biju, Akkattu T.,Poisson, Thomas,Besset, Tatiana
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Read Online
- A general, enantioselective synthesis of 2-substituted thiomorpholines and thiomorpholine 1,1-dioxides
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In the course of our drug discovery programs, we had need to access chiral, 2-substituted thiomorpholines and their oxidized congeners, thiomorpholine 1,1-dioxides. Here, we disclose a high-yielding, general protocol for the enantioselective synthesis of
- Reed, Carson W.,Lindsley, Craig W.
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supporting information
(2019/09/10)
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- Electrophilic Zinc Homoenolates: Synthesis of Cyclopropylamines from Cyclopropanols and Amines
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Metal homoenolates, produced via C-C bond cleavage of cyclopropanols, have been extensively investigated as nucleophiles for the synthesis of β-substituted carbonyl derivatives. Herein, we demonstrate that zinc homoenolates can react as carbonyl-electrophiles in the presence of nucleophilic amines to yield highly valuable trans-cyclopropylamines in good yields and high diastereoselectivities. GSK2879552, a lysine demethylase 1 inhibitor currently in clinical trials for the treatment of small cell lung carcinoma, was synthesized using this strategy.
- Mills, L. Reginald,Barrera Arbelaez, Luis Miguel,Rousseaux, Sophie A. L.
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supporting information
p. 11357 - 11360
(2017/08/30)
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- AUTOTAXIN INHIBITORS
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The present invention relates to compounds of formula (I): wherein R1, R2, R3, R4a, R4b, R4C, R4d, L, A, Q, W and HET are each as defined herein. The compounds of the present inv
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Paragraph 00360
(2016/09/22)
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- A general, enantioselective synthesis of protected morpholines and piperazines
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A short, high yielding protocol has been developed for the enantioselective and general synthesis of C2-functionalized, benzyl protected morpholines and orthogonally N,N′-protected piperazines from a common intermediate.
- O'Reilly, Matthew C.,Lindsley, Craig W.
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supporting information; experimental part
p. 2910 - 2913
(2012/08/14)
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