Enantioselective synthesis of BMS-911278: a triple reuptake inhibitor

Li, Jianqing; Smith, Daniel; Krishnananthan, Subramaniam; Wu, Dauh‐Rurng; Sun, Dawn; Ryan, Kristen; Hu, Min; Cui, Wenge; Naginskaya, Jennifer; Liu, Shuang; Lobben, Paul C.; Ng, Alicia; Olson, R. E.; Mathur, Arvind

doi:10.1016/j.tetasy.2016.12.003

Cited by 5 publications

(1 citation statement)

References 16 publications

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“…Rh-catalyzed diastereoselective 1,4-arylation of chiral diene 4a with phenyl boronic acid provided 12 in 89% yield with 87.5:12.5 dr and 13 in 95% yield with 90:10 dr (Fig. 5b ) 39 . The stereochemistry of the products was solely controlled by the chiral ligands.…”

Section: Resultsmentioning

confidence: 99%

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Wang,

Jie,

Chong

et al. 2024

Nat Commun

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Catalytic cascade transformations of simple starting materials into highly functionalized molecules bearing a stereochemically defined multisubstituted alkene, which are important in medicinal chemistry, natural product synthesis, and material science, are in high demand for organic synthesis. The development of multiple reaction pathways accurately controlled by catalysts derived from different ligands is a critical goal in the field of catalysis. Here we report a cobalt-catalyzed strategy for the direct coupling of inexpensive 1,3-enynes with two molecules of acrylates to construct a high diversity of functionalized 1,3-dienes containing a trisubstituted or tetrasubstituted olefin. Such cascade reactions can proceed through three different pathways initiated by oxidative cyclization to achieve multiple bond formation in high chemo-, regio- and stereoselectivity precisely controlled by ligands, providing a platform for the development of tandem carbon-carbon bond-forming reactions.

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Section: Resultsmentioning

confidence: 99%

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Wang,

Jie,

Chong

et al. 2024

Nat Commun

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Copper‐Catalyzed C(sp³)−H/C(sp³)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

Zhu

Zeng

et al. 2017

Angewandte Chemie

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The first oxidative C(sp 3 ) À H/C(sp 3 ) À Hc ross-dehydrogenative coupling (CDC) reaction promoted by an internal oxidant is reported. This copper-catalyzed CDC reaction of oxime acetates and trifluoromethyl ketones provides as imple and efficient approach towards 2-trifluoromethyldihydropyrrol-2-ol derivatives in ah ighly diastereoselective manner by cascade C(sp 3 ) À C(sp 3 )bond formation and cyclization. These products were further transformed into various significant and useful trifluoromethylated heterocyclic compounds,s uch as trifluoromethylated furan, thiophene,p yrrole,d ihydropyridazine,a nd pyridazine derivatives.Atrifluoromethylated analogue of an Ab 42 lowering agent was also synthesized smoothly. Preliminary mechanistic studies indicated that this reaction involves acopper(I)/copper(III) catalytic cycle with the oxime acetate acting as an internal oxidant.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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Copper‐Catalyzed C(sp³)−H/C(sp³)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

Zhu

Zeng

et al. 2017

Angew Chem Int Ed

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The first oxidative C(sp )-H/C(sp )-H cross-dehydrogenative coupling (CDC) reaction promoted by an internal oxidant is reported. This copper-catalyzed CDC reaction of oxime acetates and trifluoromethyl ketones provides a simple and efficient approach towards 2-trifluoromethyldihydropyrrol-2-ol derivatives in a highly diastereoselective manner by cascade C(sp )-C(sp ) bond formation and cyclization. These products were further transformed into various significant and useful trifluoromethylated heterocyclic compounds, such as trifluoromethylated furan, thiophene, pyrrole, dihydropyridazine, and pyridazine derivatives. A trifluoromethylated analogue of an Aβ lowering agent was also synthesized smoothly. Preliminary mechanistic studies indicated that this reaction involves a copper(I)/copper(III) catalytic cycle with the oxime acetate acting as an internal oxidant.

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Enantioselective synthesis of BMS-911278: a triple reuptake inhibitor

Cited by 5 publications

References 16 publications

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Copper‐Catalyzed C(sp³)−H/C(sp³)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

Copper‐Catalyzed C(sp³)−H/C(sp³)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

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Enantioselective synthesis of BMS-911278: a triple reuptake inhibitor

Cited by 5 publications

References 16 publications

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Pathway-divergent coupling of 1,3-enynes with acrylates through cascade cobalt catalysis

Copper‐Catalyzed C(sp3)−H/C(sp3)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

Copper‐Catalyzed C(sp3)−H/C(sp3)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

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Copper‐Catalyzed C(sp³)−H/C(sp³)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols

Copper‐Catalyzed C(sp³)−H/C(sp³)−H Cross‐Dehydrogenative Coupling with Internal Oxidants: Synthesis of 2‐Trifluoromethyl‐Substituted Dihydropyrrol‐2‐ols