Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

Hall, Thomas Howard; Adams, Hannah L.; Vyas, Vijyesh K.; Chu, K. L. Michael; Wills, Martin

doi:10.1016/j.tet.2020.131771

Cited by 8 publications

(2 citation statements)

References 83 publications

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“…All spectra were in agreement with reported data. 11 The enantiomeric ratio (92:8 er) was determined by HPLC analysis using a Chiralpack IA column, n-hexane/isopropyl alcohol 90:10, 1 mL/ min, 28 (E)-3-(4-Methoxybenzylidene)chroman-4-ol (rac-8a). 74 Compound 2a (0.2 mmol) was dissolved in methanol (2 mL), followed by the addition of NaBH 4 (0.6 mol, 3 equiv, 23 mg).…”

Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

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Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori–Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

et al. 2021

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3-Arylidenechroman-4-ones and 2-arylidene-1-tetralones are hydrogenated to cis-benzylic alcohols in dr’s and er’s up to 99:1 via a CC and CO one-pot reduction in the presence of 2–5 mol % Noyori–Ikariya-type RuII chiral complexes and HCO2Na as a hydrogen source under asymmetric transfer hydrogenation–dynamic kinetic resolution (ATH-DKR) conditions. The oxidation of theses substrates resulted in the enantioselective synthesis of the natural homoisoflavanone dihydrobonducellin and its carba-analogues.

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Section: The Journal Of Organic Chemistrymentioning

confidence: 99%

“…However, the reduction of chalcone was an exception, resulting in the saturated ketone as the major product (75%) along with the corresponding benzylic alcohol (23%) in a 93% ee. Just recently, Wills et al reported the preferential 1,4-reduction of chalcones, which was promoted by ( R , R )- 1e and a HCO 2 H/Et 3 N mixture (Scheme b).…”

mentioning

confidence: 99%

Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori–Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

et al. 2021

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Narasaka reaction: Desilylative acylation of 1-alkenylsilanes with acid anhydrides

Xiao

2021

Chinese Chemical Letters

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Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of Chalcones in Water: Application to the Enantioselective Synthesis of Flavans BW683C and Tephrowatsin E

et al. 2022

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The oxo-tethered-Ru(II) precatalyst promoted the one-pot C�C/C�O reduction of chalcones using sodium formate as the hydrogen source in water through asymmetric transfer hydrogenation. Twenty-seven 1,3-diarylpropan-1-ols were obtained in good to excellent yields (up to 96%) and enantiomeric purities (up to 98:2). Our data suggested that the enones are first reduced to the corresponding dihydrochalcones (1,4-selectivity) and then into 1,3-diarylpropan-1-ols (C�O reduction). The stereoelectronic effects of electron-donating and electron-withdrawing groups at the ortho, meta and para positions of both aromatic rings were evaluated. The 2-OH group at the B ring was well tolerated, allowing a straightforward enantioselective synthesis of two flavans through the Mitsunobu cyclization, the antiviral (S)-BW683C and the natural flavan (S)-tephrowatsin E.

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Asymmetric transfer hydrogenation of unsaturated ketones; factors influencing 1,4- vs 1,2- regio- and enantioselectivity, and alkene vs alkyne directing effects

Cited by 8 publications

References 83 publications

Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori–Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

Asymmetric Transfer Hydrogenation of Arylidene-Substituted Chromanones and Tetralones Catalyzed by Noyori–Ikariya Ru(II) Complexes: One-Pot Reduction of C═C and C═O bonds

Narasaka reaction: Desilylative acylation of 1-alkenylsilanes with acid anhydrides

Ru(II)-Catalyzed Asymmetric Transfer Hydrogenation of Chalcones in Water: Application to the Enantioselective Synthesis of Flavans BW683C and Tephrowatsin E

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