Diastereoselective copper-catalysed 1,4-addition of Grignard reagents to N-enoyl oxazolidinones

Drusan, Michal; Galeštoková, Zuzana; Šebesta, Radovan

doi:10.1039/c3ra42024h

Cited by 4 publications

(1 citation statement)

References 55 publications

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“…We tried to address this problem by changing the substrate for the enolate generation to enantiopure N ‐enoyl oxazolidones 6 . The conditions for the conjugate addition were similar to those already published on this type of substrate 25. We have found that chiral ferrocenylphosphane oxazoline ligand L3 promoted the conjugate addition with complete diastereoselectivity.…”

Section: Resultssupporting

confidence: 53%

Asymmetric One‐Pot Conjugate Addition of Grignard Reagents to α,β‐Unsaturated Compounds Followed by Reaction with Carbenium Ions

et al. 2015

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Asymmetricc atalytic multistep reactions enable the formation of structurally complexc ompounds from simple starting materials.E nantioselective Cu-catalyzed 1,4-additionso fG rignard reagents to Michaela cceptors form reactive chiral enolates. We show here that these chiral enolates react in ao ne-pot fashion with naked carbenium ions,s uch as tropylium, 1,3-benzodithiolium, andd ianisylmethylium ions.T he corresponding productsw ereo btained in good yields,w ith enantioselectivitiesu pt o 96% ee andhigh diastereomeric purities.

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Section: Resultssupporting

confidence: 53%

Asymmetric One‐Pot Conjugate Addition of Grignard Reagents to α,β‐Unsaturated Compounds Followed by Reaction with Carbenium Ions

et al. 2015

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Olefins Hydrofunctionalization; Hydroalkylation of Electron Deficient Olefins

Kisszékelyi

Šebesta

2024

Comprehensive Chirality

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Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer

et al. 2014

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The formal synthesis of (+)-3-epi-eupomatilone-6 () and the 3,5-bis-epimer () has been accomplished. The key synthetic strategy involved the stereoselective construction of (3R,4S,5R)- and (3R,4S,5S)-trisubstituted γ-butyrolactones and from (2R,3R)-2,3-dimethyl-4-pentenoic acid derivative , which was readily obtained via stereoselective conjugate addition of vinylmagnesium chloride to a chiral α,β-unsaturated N-acyl oxazolidinone (Evans' auxiliary) followed by α-methylation.

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Diastereoselective copper-catalysed 1,4-addition of Grignard reagents to N-enoyl oxazolidinones

Cited by 4 publications

References 55 publications

Asymmetric One‐Pot Conjugate Addition of Grignard Reagents to α,β‐Unsaturated Compounds Followed by Reaction with Carbenium Ions

Asymmetric One‐Pot Conjugate Addition of Grignard Reagents to α,β‐Unsaturated Compounds Followed by Reaction with Carbenium Ions

Olefins Hydrofunctionalization; Hydroalkylation of Electron Deficient Olefins

Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer

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